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All the Shoes & Boots Derek Guy Loves—and a Few He Really Doesn't—From Bespoke to Workboots

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All the Shoes & Boots Derek Guy Loves—and a Few He Really Doesn't—From Bespoke to Workboots

Stitchdown Expo 2026 in Chicago will offer a rare, hands-on experience with over 50 global footwear makers, featuring live shoemaking, expert sizing, and the chance to try on finished shoes. The event will also partner with Superdrunk to highlight premium dress footwear and community culture. In a deep-dive conversation with menswear writer Derek Guy, the focus shifts to the value of craftsmanship—particularly in hand-sewn moccasins like Townview and Arrow—whose traditional, small-scale production is vulnerable to collapse. Derek advocates for mindful consumption, urging fans to buy now before these artisanal traditions vanish. He emphasizes that comfort and fit matter more than style, citing the unique footbed and moccasin construction that adapts to the wearer’s shape. While brands like Jam Weston and Paraboot are praised for quality, their sizing can be unpredictable, especially in European markets. Derek highlights the importance of in-person fitting and trusted makers, such as Nicholas Templeman and Seji McCarthy, who offer made-to-order services with attention to detail. He also champions bespoke workwear and styles like split toes and tassel loafers, which reflect a more authentic, timeless aesthetic. Ultimately, the conversation underscores a deep appreciation for craftsmanship, tradition, and the human element in shoe-making—a response to the decline of artisanal industries and a call to support sustainable, high-quality footwear.

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Hey, Ben from Stitchdown here. Wondering what you're doing on November 6th and 7th, 2026? Because if it's not coming to Stitchdown Expo 2026 Chicago at artifact events, it pretty much needs to change to coming to Stitchdown Expo 2026 Chicago at artifact events. Once again, we'll have 50+ quality footwear makers, tanneries, and plenty of other crazily high quality goods from around the world. Yes, you can meet the people behind the brands and trust me. They want to show you how they do what they do. Live shoemaking and repair will be happening left and right. You can even try it yourself. In terms of finished shoes and boots, literally, nowhere will get you this kind of chance to actually handle product and more importantly, try things on while getting expertly sized. Stop buying shoes that don't fit. Come to this thing! For 2026, we're also teaming up with the Superdrunk team to bring in some of the world's best dressy footwear and everything that goes along with it. And of course, we'll have parties each night so you can hang with the best community out there and the folks behind the brands. Head to StitchdownExpo.com for more info on the whole show, tickets, all of it. See you in Chicago. OMG, it's Derek Guy. Derek's an OG forum junkie turned menswear writer for Put This On, mass publications like The New York Times, and his own always excellent blog, Die Workwear. In the last few years, Derek has become to many menswear guy on Twitter, where sharp cultural insights on style and complete lack of brevity break every rule of the platform in such a wonderfully potent manner. And sometimes get him screamed at online, believe it or not. I've been a huge fan of Derek's for years, so getting some time with him to just talk about the shoes and boots we dig from bespoke to work boots was putting it quite lightly and honor. Derek and I actually taped two episodes, you'll hear more about the second soon. But this one, I love so much, I loved it. This humble shoe cast started back in 2020 with a couple of guys just talking for far too long about the shoes and boots they loved. Love you, Teach-O, and this episode with Derek is a really splendid return to exactly that. This is actually our final episode of season 14, but we'll be back soon and we'll be filling the void with some great subscribers only bonus episodes. More info on how those bonus episodes work and how you can support the shoe cast can be found at stitchdown.com. So now here's Derek guy on the shoe cast. How's it going, Ben? So we taped an episode a few weeks ago, but I don't know which one's going to come out first, so thrilled to have you on, slash thrilled to have you back. I thought we might simplify things a little bit today and just kind of have you and me ramble endlessly about shoes and boots and whatever, styles, brands, maybe we talk about some lasts, what you like or maybe don't. Maybe what you think is good to like wear with some of it clothing wise? Solid marriage stuff is what I'm getting at here, is this a decent plan? Sure. Let's start with what are you currently wearing on your feet and do you like them? I am at home since I am Asian, I don't wear outside shoes in the home, so I'm currently wearing a pair of town view moccasin slippers that I use as my home slippers. And those are like your daily, I'm home now, I'm wearing the town views. Yeah, I bought a few, over the years, I've tried various shoes for home kind of use, so one pair is a pair of, I think they were, if I remember correctly, they may have been Derek Rose or by one of those companies that sell slip on shoes and the Piccadilly Arcade or something like that, they're kind of like gentlemen shoes, if you will. And I originally bought those because I was like, oh, those, those seem fancy, like that's what fancy people wear at home, but they're not that comfortable. At least the ones that I bought weren't that comfortable. And so they have gotten almost nowhere. But the town view moccasins I find extremely comfortable and actually only get more comfortable over time. They end up having to be in such disrepair, like I have, my foot has to be like coming out of the other side for me to stop wearing them. I once asked Nicholas Templeman who's a bespoke shoe maker, former last maker at John Lobb, now an independent working under his own own name, if it was possible to get a pair of normal dress shoes made with the kind of like footbed that I get in my town view moccasins, because I've never gotten the footbed that I've gotten in my town view moccasins. I've never had that in bespoke shoes, which are, as your listeners, no hand wilted or even good your wilted shoes, which famously have that cork kind of feeling that's supposed to take on the shape of your foot. I've never gotten the amount of shape that I've gotten in my town view moccasins. And town view moccasins, as you know, are made, I mean, it's a moccasin construction. So you know, the top basically curves around to the bottom. And then I think they add maybe one or two extra layers of, I believe someone would have to go to their website to double check, but I believe it's like bowl leather or something. So on the bottom. So it's basically imagine that's like basically the soul, if you will. And I think with all of those layers of what I believe is bowl leather and then also it's deer skin lined, it not only quickly takes the form of my foot, but it has an even deeper impression than I get in either hand wilted shoes or good your wilted shoes. And I don't know. I've never been able to get that in a pair of normal shoes. Nicholas, you know, we discussed it for a little bit and he was like, yeah, that's just now, you know, like normal shoes are made and I didn't want to like press them on experimenting with anything else because I pay full price for my orders and I would not want him to, I would not want to be the guinea pig and then finance that. So, but whatever Townview Moxton does, they're incredibly comfortable after, I would say, you know, like with all shoes, like they're okay when you first slip them on. But man, like after six months or a year, they're like, you wish you were wearing those all the time. Oh, yeah, I mean, I do wear an encourage wear of shoes in my home. I also have six year old and a four year old, so like there's all sorts of shit on the floor. There's no way around that. Yeah, I'm also kind of generally wearing like some kind of moccasins, like Russell moccasins or whatever, whether I was wearing them during the day or not or some Berkensaks, Berkensaks Boston's, which I do feel provide some level of orthopedic benefit, I think. Yeah, I mean, they famously, they're famously kind of molded to your foot, right? I like the look of them, especially when they're styled in cool outfits. I met when I tried them on, I was like, this is like insanely uncomfortable. I assume they get more comfortable, but like in the beginning, it's like standing on concrete or something. Am I wrong in that? They're standing on concrete that have like little other concrete ridges like right under your toes. So your toes can grip the concrete when they're new. Yeah, no, they, I'm actually like probably sent as many DMs about like why are my Berkensaks not breaking in is like other stuff, which is interesting because it's like not my specialty, but yeah, they're like kind of terrible at first. I remember the first pair I got like way back in high school, you know, there, there was an internet, but I think this was just when like people told you things, they're like, all right, so you go down to the beach like saltwater is better and you just stand in it 10 minutes and then you wear your Berkensaks and like it'll be a lot better. And I did that and I wouldn't recommend it necessarily, especially in saltwater or kind of anything. It didn't kill him like eventually oddly somebody stole that pair of Berkensaks or possibly mistook it for theirs. I was like playing in a sports game and over the summer and bore them to the field and then they were gone and I had to drive a manual transmission car home barefoot. Wow. But yeah, they are kind of tough at first, but they don't take terribly long. Like you forget about it and then they're worth it once you get them there. Yeah. Yeah, as I mentioned to you, you know, I kind of hurt my back recently, so I'm trying to do like a lot of standing instead of sitting. I've been like standing in them, I'm like this, this seems like the medically appropriate approach to just standing, I guess. I'm on the town view site, yeah, you're 100% right, they have, so again, moccasin construction which is different than a hand-welted shoe or a good-your-welted shoe where there's like a big, thick slab of hard leather that everything has to attach to under your foot, like, you know, the moccasins wrap under, you know, that's the vamp, vamps on top on a welted shoe, but that's the vamp, which was once explained to me, I think by Yuki Matsuda that at least how he thinks about it, but, you know, maybe from a technical perspective, that the vamp is simply, you can point to all sorts of exceptions on this. This is the largest piece of leather on a shoe. So that's where all the leather is on a moccasin kind of going underneath, and therefore it's called a vamp. I don't know 100% how accurate that is, but it really stuck with me. Yeah. So yeah, the vamp here is cow hide, and then there is what they call their double sole or you sometimes here referred to as a molded sole underneath, which is that bull hide. And then I don't know how many moccasin makers do this. They throw another level of leather in between the two of them for added comfort, as they say. Yeah, they're supremely comfortable. There was a moment I think it was during the pandemic during the 2020 lockdowns. I read somewhere that the I believe arrow moccasins was run by someone, and I think maybe either sold the company to someone or his son took over, but whoever was running the company of the time was not the original founder. I believe I could be wrong. But the person who had owned it in 2020, I believe, passed away. And I remember reading that news and I was like, man, that's crazy. And I suddenly realized that I love the whole tradition of like hand-sewn moccasins in Maine, that whole cottage industry. And I realized a lot of these companies are hanging by a thread. It's just like the old kind of like sartorias, bespoke tailoring words, it's one person running the shop. They probably don't have an apprentice. And then once that shop is gone, it's gone. So I ended up buying a bunch of town view moccasins at that period. And I just have them on shelf, put on ice, and that I'm hoping that will last the rest of my life. So yeah, if people are also in love with that kind of, I mean, craft is such an overused term. But whatever you want to call it, that tradition of hand-sewn moccasins, I think town view does a really good pair. I think we can continue to apply the term craft to like actual craft. I think that's fine. Yeah. Yeah. They should have been able to like run it off of that, which is like, that's exactly what it is. And yeah, I think you're right. I think arrow is like just done. I'm pretty sure town view is, yeah, the kind of brand quote unquote, but really like incredibly small operation that for whatever reason, right? Like personal choice or obviously kind of worse things, yeah, it could just kind of vanish. The original people at town view was a couple, an elderly couple. I mean, there were an elderly couple when I first bought mine like 15 years ago. And the train, the sun went into the family business and the sun was operating under a different banner for a while. And I believe, I don't know for sure, but I don't think the sun's business is still operating on the banner. And I suspect that he may have been folded into the families, you know, kind of operation banner name. I don't really know. But again, it's one of those things, you know, like, I don't know if the parents are still making shoes. And maybe one day the sun decides it's more profitable to, you know, do X, Y, Z or something than that would be another loss. You're totally right about just that tradition up in Maine and, you know, I think arrow was maybe in Massachusetts, yeah, maybe, you know, kind of similar lineage. I remember we did a podcast of us a way back like four years ago now and it was about kind of tracing what the main footwear industry was. It was like greatly informed by series of chats that I had with Kyle Rancourt, really chronicle just an absolute ton of, you know, this rise and like literal cottage industry, which is, you know, that's what's cool about arrow and town view where it was like, you know, the cottage was either an actual cottage like just your house, right? And that all fed into this kind of wealth of overall shoemaking. And then, you know, kind of like a brand type situation emerged with like a quaddie. And then obviously later Rancourt and like Rancourt was doing production before they were themselves a brand for spary and others. And then, you know, it was about this kind of decline, right? In terms of obviously outsourcing, Warren Buffett purchasing Dexter, which was like far from exclusively that kind of footwear, but it was definitely a part of it, which Warren Buffett is called the worst investment he ever made because like shoes are an abnormal business, basically. But like that had a huge impact and then all the supply chain stuff. And then like at the end of this episode, it was like, but look at this comeback, look at all these positive things that are happening. And like I would have to record another like decline episode, like quite unfortunately at this point in terms of like main made footwear. It's rough. Yeah. So yeah, buy them up. Yeah. I mean, not to encourage, you know, wasteful consumerism. But if you're standing on the fence, I would say, you know, things, from what I've seen, things, you know, things disappear. I think we are all in love with something that is on an obvious low decline in my opinion. So again, not to encourage wasteful consumerism, but I do thank you for on the fence. It's always better to buy it now than put it off. Hey, there are a couple hundred bucks. How do you size them? Let me check. Give me a second. I have them on my feet. I went through the size. So yeah, take your brand off size. Okay. And I encourage you, if you're, I think they offer unlined and lined in deer skin, I believe. I encourage you to splurge for the deer skin lining. I think they are a bit more comfortable that way. Not blind wasteful consumerism, but I might have to do this thoughtful wasteful consumerism. Yes. Yeah. I'm not going to throw them out. That would be crazy. On the moccasins side of things. So like looking at town views, you know, I'd call them like a camp mock. I think that pattern wise, it's, it's safe to call them that, which probably I think a casual shoe purchaser could like easily be confused with like a boat shoe or a ranger mock, which are kind of like the three, you know, core main styles that I can think of offhand. Do you have like an affinity specifically for that pattern? I bought a bunch of camp mocks years ago from like all of the various producers. It's been a while. I think if people Google camp mock put this on, they'll find a bunch of articles as well as comparisons of different brands. I did wear those for a while. I admit my wardrobe has kind of drifted away from the stuff that I would normally wear with that. I wear a lot of workwear and tailored clothing. So camp mocks, I guess you could wear a camp mocks with workwear. I just don't. I just normally wear boots or sneakers, but I do like the camp mocks and I do like trail mocks. I admit I don't like boat shoes a little bit too preppy for my taste years and years ago. Like I think like 20 years ago, I remember I bought, it was not even that preppy, but I bought a sir single belt and it just never got anywhere. And I realized I'm like, I'm just not that preppy of a dude. So a lot of those things that are super preppy, like boat shoes, sir single belts, certainly needle point pants. So I never bought those. A lot of those things just don't make it into my wardrobe because I don't dress very preppy. But I did like camp mocks and trail mocks for a while with like, you know, like a simple pair of jeans or five pocket cords and a shetlanded and Oxford button down. I think that's still a good look. It's just that I don't really wear those, that kind of casual wear very much anymore. Yeah, I generally like that stuff. What do you think makes a boat shoe that much preparer? It's association with really preppy people, you know, I remember for a while, for a very short while, I screen shot it because people leave insane comments on mentor blogs and forums. No, surely that is not true. The best is if you go to, well, certainly the Wall Street Journal used to have it. I don't know if they do anymore, but if you go to those main, like if you, if you break the menswear bubble and you go to wear like normal people read, you know, like style articles, like New York Times, Washington Post, Wall Street Journal, some of those online sites will have a comment section. If you go scroll through them, they're always like the most insane comments. Now, for a while, I was, I was screenshotding all of the insane comments that would come across and I was one day planning to post a post to put this on of like insane comments to menswear articles and blog posts. But one favorite one was Simon Crompton's blog, permanent style, where he had talked about a pair of boat shoes, and I don't even, I don't know. He was like, I think these are well made or good value or something. And then somebody went in and was like, those are not real boat shoes, you know, you would slip and die on a boat. It's just like the most annoying, I hate, I hate those kind of comments like, shut up. Like, yeah, these are not proper boat shoes, the deck and blah, blah, blah. And Simon was like, well, I'm not going to be on a boat. Like this is obviously something that I'm just wearing around town, like a normal, you know, like how most people use boat shoes. And then this person left the comments like, well, your life is not complete without a boat. I'm standing on my boat right now. And I was like, that is exactly why I don't wear boat shoes. It's just like, look, I'm posting this from my uncle's boat, okay? Yes. So annoying. Yeah, I just find boat shoes just a little bit too preppy. You know, like I think if you were going to wear boat shoes, there are, I have seen really charming outfits involving boat shoes. They're often like older men, you know, like full-cut khakis and a full-cut button down. And some of them look really good. My friend and podcast co-host, Peter Zotelo, visited, I think it was his uncle's home or something, or maybe a friend of his uncle or someone that he knew. He went to his home and this guy was wearing boat shoes, full-cut khakis, a hat with his all-mawder and, you know, like a button down. And he looked, he generally looked really stylish. But I do think that there's like a younger version of that that I find, at least not asked, it's not how I aspirationally want to identify or dress as. Yeah, and that's why I don't wear boat shoes. I feel like growing up like everybody just had boat shoes, so they weren't necessarily connotationally attached to anything. Wow, I did not grow up in an area where anyone had boat shoes. I did grow up in a magical place called Long Island. Okay. (laughs) So like there are boats, you're never more than like 25 miles from a boat either north or south. Maybe that was part of it. I thought it was everywhere. We definitely know when I knew wore boat shoes, but I didn't see them when I was growing up. I would think that if anyone wore them, they would be like a preppy guy, but I didn't grow up around that many preppy people. I, a friend of mine, a dad owned a boat, actually. I remember going on my friend's dad's boat one time. A man who was living. - Yeah, but other than that. - Did you slip and fall? - I don't know, I didn't slip and fall. I was kind of, I don't remember what I wore on the boat, but yeah, although I did like some preppy stuff back then. I liked Nautica and Tommy Hill figure in Polo Ralph Lauren, but they were kind of worn and, I mean, at the time, we did not aspire to dress like perhaps. It was just kind of a streetwear kind of thing. Yeah, even though they had boats on them on the sweatshirt. - What about split toes? You like split toe, you know, like a split toe derby, something like that, right? Am I wrong about that? - Yeah, I love split toes to get a little snazier. - I don't know if they're snazier, but I do love split toes. I would say that for most people will be coded as old man-ish. I like split toes because a lot of the guys that I admire in terms of style wear split toes. Yuko Akameen wear split toes. He's a figure in the Japanese men's. We're seeing known as a vintage shop and custom clothing shop. And I've been following him since like early 2000s. And then Bruce Boyer obviously wear split toes. Yeah, just a lot of the guys I consider really stylish wear split toes. I like them for that reason. They also, I like the fact that they derive from a kind of workwear history. They, John Lobb, they're called, I think nav shoes or nav derby or something like that. It comes from when people who worked on waterways wore them. And I also like them because Nicholas Teppleman once told me that I don't know if he's just kind of blown smoke up my rear end or something, but he told me that they are among one of the harder styles to make. So I appreciate them for the craft element. But you know a kind of a derby is a pretty plain shoe unless you get something on it. Like if you just think of a plain toe derby. - Just a shoe. - There's like nothing really going on. So a wing tip feels a little too gentlemen for my taste. And then of course you can put an apron on it or a lake or something. And I like that. But to me, if you can put a split toe on it just makes it a little bit more of an aesthetically pleasing shoe, especially if you can get that kind of reverse split and lift stitch. I don't like the split toe when it's a machine stitch because to me that looks a little taxidermic. But if you can get the reverse split and lift, it just looks nice. But I recognize that it's a bit of an old man shoe. But I think anyone who reads my cider follows me to any degree. Like to me, old man-ish is a plus. I like tassel loafers, I like split toes, I like baggy tweed jackets, I like drape cut suits, I like all that stuff. So to me, the fact that it's old man-ish is a plus, not a negative. But I can understand if someone is like 22 years old, they may not have that same aesthetic goal necessarily. I'm all in on the old man thing. OK. I'm trying to go through it. But I think the only pair that I still have of split toe shoes is some paraboot avanjans, which around the time that I started covering footwear and not just liking it about six years ago. I remember I was just kind of like bopping around shops in New York City, taking pictures, right, making some content, but also just like trying to talk to people and learn what they knew. And I ended up in-- I'm pretty sure Drake's is in a different location in Soho now. But I remember I was in there, and I just kind of fell in love with these paraboots. And I was also like, you know, I'm wearing aldons and red wings and that kind of stuff, like I need to, you know, what I would say is like snazz myself up a little bit. And they're like kind of chunky and funky, and like I can't seem to like get away from that in terms of my own personal taste. I wore them a ton back in the day in like those paraboot soles that they make are so comfortable and spongy and like kind of have like that bigness to them, but it's-- I don't know, there's more like squish available. Like a big soul if it's like the right material. I was wearing them a ton in the city where I don't live anymore, and I busted them out for at least the first time in like a year maybe, the other night, and I was like, man, I just love them. I gotta start wearing them more. - That's a great model from the company. I think those look really good. - They just fit me well too. What's the sizing like on those? - I sized them. I'm a brand new 11. I think they're a 10. They were trying to put me in a nine and a half and I ended up getting tens, and I kind of wear them with like a thicker sock, and you know, there's some wiggle room, but I'm not all sliding around in them. - That's a 10 in your US size. - Well, it's 10 in paraboot sizing, which is I guess UK sizing? - Yeah, okay. All right, that's how I take them. I think you could go down a little bit further, but that last is like, there is like a fairly serious taper to it compared to a lot of stuff that I wear. My toes just kind of aren't used to it. Like I generally like a nice big round last. Should still have some kind of shape to it, unless it intentionally doesn't, but yeah. So like I just, I didn't want to be like crammed in them, but like I can't fit in the Michaels, at least at the same size, which really bummed me out. I got this super cool pair. The Michaels for those who don't know paraboot's now, especially I was at like all the market week stuff last week, you know, fairly ubiquitous, especially kind of for that scene Tyrolean shoe. And I got this pair of, you know, kind of almost natural like veg tan. Basically I was like, and I love that kind of leather, and hope to wear them a ton, and just get them looking really cool. And like I just couldn't do it. Which is weird, 'cause it's like a much rounder last. You mean the Tyrolean type style, that style? Yeah, they just, well, that particular shoe, like just it didn't fit, they were like horrifically uncomfortable on me. Maybe I could have used a half size up or something like that, but I figured because of the, I think it might be a slightly shorter last. I don't want to like say that, and then have people like go and buy something online incorrectly. I will say like my information on them is incomplete compared to other pair of bootlasts. But I figured I was like, oh, this one's nice and round, you know, this will be even better. And yeah, this couldn't do it. I had to sell them eventually, and I was like, I was pretty bummed out about it. What about those? Like a Michael or, yeah, that kind of style. Yeah, I love those Tyrolean shoes. I admit I'm not crazy about this whole thing of people wearing it with like suits that I've seen. It feels a little bit hashtag mensweary, but I like them with workwear, and I like them with casual wear. I think they go great with like brands like Captain Sunshine or, you know, like any kind of, any kind of workwear looks good with it. They are admittedly in that category of like kind of funky borderline ugly, but I think they're very charming. I have a pair from, I'm trying to remember the brand. Whatever is the brand that no man walks alone cells, I don't think they sell a pair of version, and the name escapes me. But I bought my pair off of no man walks alone in Hesheng. I don't think there's a from Hesheng, but I mean, they do them every year. It might be paired with, I don't remember. Yeah, I like them. There's a cheaper variant that I think is sold at Namu shop, and NAMU, I don't know if that's how you pronounce it, but it's Namu, and it's slightly cheaper if people just want to experiment with the style. The only thing is that I find that many of these French companies are very hard to size. So that's why I asked you about Parabute. I found J and Weston very hard to size, because some of these French companies have like an internal sizing number, they have a EU sizing number, UK sizing number, US sizing number, and it just gets very weird and confusing. So I think if you buy them, you have to buy them from a place that allows for easy returns. - Yes, definitely. Okay, so I'm on Namo now. This is perfect because I saw a bunch of these Clemons, I believe, is the pronunciation on that, which is what they have. Yeah, kind of this classic French Tyrolyne Chou. And yeah, it talked with, I think the son of the founder, but like the grandson or great-grandson of the factory that was making them before they started their own brand, Clemon. And he had everything for like next fall, I guess, that they had, so it was like a nice wide range and they had a bunch of other styles too, but obviously, this is kind of one of the core ones. The interesting thing about them, which I did not realize is that they're actually not a welted shoe, it's a cemented shoe, but you can get them for like a couple hundred bucks. I think they're on Namo, they're 260, it looks like. So it really helps them keep the costs down, but like the materials were good. They had these really cool ones that actually posted on my Instagram that were, it looked like they were corduroy fabric, but it was like corduroy suede, basically. Did I really like it? And I think it was maybe even like a two-tone or like a different texture on there too. So yeah, like I'm quite impressed with them. You know, like I'm not usually recommending kind of non-welted cemented shoes to people, but for the price and like that kind of style at that price, you know, it's a good way to like test something out, I would say. Yeah. To your point earlier about the lineage of these things, what the factory that makes the Clemens was doing previously was government contracts, pretty sure he said like police shoes were part of it at certain points in time, but railway workers. So like if you worked for the railroad, I think not necessarily doing heavy labor, but like checking tickets or driving the train, this is what they all wore and they were issued them. And like obviously as a factory, it's like great to have those contracts. And I was like, huh, okay, like is there a reason for that? This type of shoe, you know, does it function in a certain way for a railroad ticket checker? And you know, we kind of moved on in the conversation after he gave me the, couldn't really quite tell you look. But I found that pretty interesting, regardless. Nice, yeah. So yeah, those are cool. Wait, so what about Jam Weston? I love Jam Weston. I absolutely, Jam Weston golfs are maybe my favorite, I don't know if you would consider them dress shoes, but like, you know, casual, nice shoes that I've ever had. I have a couple pairs and I wear them as often as I can. - I love Jam Weston. I mainly like their 180 loafers. But again, super hard to size, strongly, strongly recommend buying from a shop that gives both sizing of ice and will take returns. But I really like the high wall Jam Weston 180 loafer. I think that can be worn with like contemporary casual wear from, you know, you could wear that with like orally, for example, would look great. And also works well with like obviously classic tailoring. Their golf shoes are really nice. They have that, was it like the half hunter or full hunter? The name escapes me. - The demi chas. - And then the chas. - Yeah, the demi chasens, the chas. Those I found a bit hard to wear. I tried them on in store back when they still had a flagship in New York City. I found those really, really hard to wear. So I ended up getting a pair made through Nicholas Templeman that's inspired by the demi chas. But the full like Jam Weston demi chas in full chas, to me is like just like really loud, visually loud shoes. So yeah, but otherwise the 180 is great. The golf shoe is great. Bit expensive. They are better to get in Paris at least. - Oh, is the cheaper in Paris? - Yeah, yeah, they'll be significantly cheaper. I mean, they're really difficult to get in the states now. That store was, I love that place. And it was there and they had shoes and you could buy them and try them on. It was incredible. But yeah, that was their only US location. I mean, I'm sure you can get them from like Mr. Porter or something like that. - Of course, the problem with buying any kind of slip on is the 180 is unique and that the sole is, I remember, if I remember quickly, it's a bit thicker and a little bit stiffer therefore as a consequence. Whenever you're trying to slip on, there's gonna be some heel slippage because you haven't broken in the shoe. - Yep. - But especially with the Jam Weston 180 because the sole is a little bit stiffer and a little bit thicker, I found it really useful to be able to go into a store, talk to a sales associate, get the right sizing and have them help me figure out if fit well enough that it would fit my foot once the shoes were broken in. Whereas if you're buying and you're trying them on at home, you know, there's gonna be some heel slippage because it's a slip on and it's a fix ol' and then I think it'd be hard to know whether or not you have the right size. It's really a shame that they closed their store 'cause I think that kind of in-person service is really useful. Maybe, I don't know if maybe LaFoe carries them or something but I would always try to find them through a store 'cause you probably are gonna need help not only finding the right size but someone to figure out whether or not the heel slippage is acceptable. - Yeah, I don't think Steven has them at LaFoe. I don't think, they sell it on issues in France and that's obviously where their focus is. But yeah, that shop was great and the guys in there like they were just kind of honest about everything. They weren't just trying to get you out the door with a $800 pair of loafers. Like they would help you understand that. So yeah, it's like, it's a tough loss and I remember being quite sad. When it happened, especially never having, taking lots of pictures but never having, you know, try it on and/or purchase the triple sole 180s which just lodge in my brain. It's like, okay, so you got that extra thick sole. Let's do it three times. Eventually, I was in Paris a couple of years ago and I was like, this is what I'm gonna get. Like I was hell bent on buying a pair of shoes. I thought long and hard about going off plan on the triple sole 180s because I was in Anatamika and they have all those modified last aldons. Like boots, including in patterns that they don't offer to anybody else with this really cool backstay on them. All in Shell Court event, they had tons of sizes like a modified last molded shoe in New York City is kind of the US home of them and like just an incredible shop. Anybody who's ever in Midtown, Manhattan, go see Ron at molded shoe is an absolute time capsule. I love it, but he doesn't have like this kind of stuff and then I ended up getting these triple sole 180s that really like a lot of pain was incurred in my attempts to break them in and some blood and I might even cry once. Probably more for the shoes than my injuries, but yeah, they look great on the shelf, just really an incredible feat of shoe making visually at least. I don't regret it, I don't regret it. - What else on like the loafer front? What are you, you know, feeling personally or just stuff that's out there? 'Cause I feel like like loafer madness is not subsided and I like that. - I mainly wear penny loafers and taffos and loafers. Penny loafers, I really like Edward Green's Piccadilly. I think that just took our last goes really well with tailoring, bit pricey, bit expensive. So someone was looking for a more affordable alternative. I would check out Carmina and Miriamen. Obviously those are names always passed around. TLB Mallorca I assume probably has something that is kind of in that Piccadilly shape. I assume I don't know their inventory offhand at the moment, but they offer really good money for value. But I do like the Edward Green Piccadilly and Dark Oak if you wear suits and sport coats. And my go-to shoe actually for tailoring is a black tassel loafer that Alden made for Brooks Brothers way back on the day. Their version of the tassel loafer is their normal tassel loafer, but they put a bit of what was called foxing at the back, which is really just a stitching detail at the back. I think that looks really nice. And I love the fact that these kind of two American giants collaborated to do something. Unfortunately they cut the, I don't know who cut ties, but Alden no longer manufactures for Brooks Brothers. I have to assume Brooks Brothers cut the tie. But you can get the tassel loafer without the foxing directly from Alden. I really like those in black, surprisingly. I find black tassel loafers are super easy to wear with suits and sport coats. A friend of mine put it really well is that you can wear black tassel loafer any time that you can imagine a black knit tie in an outfit. And I think that's generally true. The only outfits I find that black tassel loafers don't really go well even though a black knit tie works is are like really light colored tan summer suits, like tan linen or tan gabardine suits. I think that looks a little bit better with a mid-brown shoe because you're lowering them. amount of contrast between your outfit and your shoes. I like those, and then obviously Alden leads your handstones. I think that is like, with tailoring, it's a little bit like you have to accept that it's a very round toe kind of trad shoe, but they also work really well with casual wear. I think Alden's leads your handstones work really well with jeans. I like them best in suede, but you know, they're also available, I think in shell-court of fashion and Calfskin, but I think in a mid-brown suede, those look really good. What else for loafers? I think I was at my friend's Peter Sotello's house, and he recently bought the Kilti loafers from Doc Martens that he said everyone in, I think he was at a fashion show event week in London. He said everyone was wearing those and he thought they looked really good. Yeah, they're pretty cool. I was looking at those for a while. They're a little, you know, like you have to, they're kind of like a fashion shoe essentially. So I think you have to like have the right outfit. As he explained it to me, they offer both the corrected grain leather version and a full grain leather version. The corrected grain, people can just go on the site and look, it's just a really chunky, you know, that kind of like chunky Doc Martens sole, that rubber sole with the ridges on the side. And then the full grain leather version has is basically the same except it's full grain leather, but it has the yellow stitching, which is obviously a trademark of Doc Martens. I admit the leather quality on the corrected grain, it's like, you know, if anyone has ever handled Doc Martens or grew up at Doc Martens, like you know what I'm talking about. It's like this really thick, plasticky, unapologically plasticky kind of leather. I have not handled the full grain version. I think if I were to, I wish they came out with a version that was full grain and without the yellow stitching, because I think that would be easier to wear, but they did look really cool. What else are some styles that are good? Those are basically the ones that I wear most. I'm currently having a pair of tasselofers made through Nicholas Tumpleman. Nice. And I don't know if it counts as a slip on, but I'm also having a pair of single monks made through Seji McCarthy. Oh, no way. Really a slip on because it doesn't have laces. So yeah, those are the slip ons I'd mainly wear. Will you tell me more about these Seji McCarthy shoes? Well, he has a couple of services. One is, if I remember correctly, Seji, if he's listening to this, you know, feel free to correct me. I definitely know that he has a full bespoke service. He'll basically make you, you know, a bespoke shoe as, you know, like bespoke shoe making goes. And then he has essentially what is kind of like an MTO service where he has a pre-made last that he'll fit up as your listeners. I'm sure no, pre-made last and then they'll fit up your last by either placing wet leather onto the areas that need more room or they may shave certain areas. This has a kind of certain limitations because sort of I kind of liken it to drafting a pattern off of a block in tailoring. So in tailoring, you can either draft a pattern from scratch, which is what it sounds like. You're either very few tailors do this nowadays, but some tailors still freehand it. That's called rock-of-eye. But most tailors will use a formula when they're drafting from scratch and then they can create your pattern using some kind of drafting method. But other way to draft the pattern is obviously to have a pre-made block and then you adjust it using the person's measurements. But you can only change the block so much before you throw off proportions and whatnot. And I think it's kind of to the degree that you can draw a analogy. It's kind of like that when you fit up a last. You have a certain style, so the gaseon girling does this as well. They have a certain style that pre-made last and then they'll fit up the last depending on where you need room or where you need less room. So Seji has the same thing. He has a set of pre-made lasts and that he can turn into styles that he's already determined. And you can, I can't remember all of the customization options, but to give an example, when I was at a trunk show, he had the samples out. And I already knew, I went into and I already knew, I want the single monk that you make because I like the way that you have designed it. I like the placement of the strap and the dimensions. And I knew that I wanted that specific shape. So I went into it knowing I want that specific shape. I don't need you to create a completely new last because that actually introduces a level of uncertainty because now I have to communicate the shape in my head to you. And then presumably once that shape is created, I have to put my foot into the already kind of half made shoe and hopefully look good. But since I already knew that I like to certain shape, I could just try on the samples that he had. He could take a look at it and say, oh, well, you need less room here or your foot pronates and we need to do this to the last. So I just tried on his sample shoes in my brand size. He took a look at how the shoe fit. He took all the notes and then he figured, okay, well, I have to adjust my pre-made last to make your shoe. And then I'll do it according to the pattern that I've already decided for for the style. So that's his MTO service and of course the MTO service is less than the bespoke because it involves less work. There are some bespoke makers and I don't know if said she does this, but I vaguely remember that he does is that some makers will also give you different price points depending on how much handwork you go into your order on the bespoke line. But I just end up going with the MTO service and as long as it's hand-welted and of course it would be hand-welted because he doesn't own factories, all made in his workshop. I don't particularly care if the other details are hand-done or not. I just wanted, I knew I like that style, I knew I like the shape and I vaguely remember the price being slightly north of Edward Green, which I thought was pretty good for that. I thought it was pretty good. Good crazy. So yeah, I was pretty happy with it. I was in Tokyo last May kind of doing like bootier stuff, there's a ton of it over there and making some videos but then I had essentially an off day. So I was like we're going to do like shoes today. So I went to super eight shoes, which is surely one of the great in the world vintage dress shoe stores run by this guy Gucci, if you're ever in Tokyo, I would strongly recommend going in there. It's like a museum, but like you know also a cobbler shop. Like not arranged as a museum, there's just like shoes everywhere but I mean he's got stuff stretching so far back and these brands that I had never heard of before and I'm pretty sure a lot of the shoemakers will go in there for inspiration and research and I saw Hero Yanagamachi. Oh yeah. I love this stuff. Incredible time and I've always been lucky enough to get a couple minutes with him when he's at LeFo in New York, usually about once a year, but like people are buying expensive shoes from him and getting measured so I don't bother him too much so it was incredible to have like a couple hours with him and then I went and saw Seiji at his shop and yeah I mean his stuff is something I don't know in any bespoke shoes or even you know any made to measure, made to order something produced by somebody who makes bespoke shoes. But yeah one day if and when that happens, I think that his long wings just speak to me in a different way than anything else that I've ever seen where I like I called them gun boats. I was like alright let's talk about these gun boats, he's like well they're not really gun boats and then explaining why because you know proportionally they're different than what he sees is you know kind of that classic American just big hunk of broke shoe down at the bottom and like he's right like you know retracted my comment but they're incredible they're like they're absolutely beautiful and it's a fantastic setup that he has there. He kind of got to like you know like many things in Tokyo kind of find the shop a little harder than you think you might have to but I think he had like a sign out on the street and yeah I think I'm I'm excited for you for those single monks I think that his work is just it really hits me you know there's a lot of fantastic shoe makers in this world but yeah I think of them as elevated Alden he does American style really really well. I've never really been super into super sleek shoes like continental kind of spoke shoe makers or even like the sleeker British shoemakers I've always wanted a slightly rounder slightly more conservative last even for dress shoes. So said you stuff really speaks to me because it's you know when I when I saw him for the first time in San Francisco he said that he took style wise in a general sense he takes love inspiration from Ralph Lauren and I was like oh well that makes a total sense because I that's like to me like the genesis of my interest in clothes yeah he I believe he trained under a hero he did and I think of him as just doing a slightly more American version elevated Alden but in a in a in a custom way and I just love his references his aesthetic reference points. Like, yeah, that kind of like classic Americana thing that you can wear with a Tweet Jacket and, you know, kind of with court trousers. Yeah, God, I'm like just looking at everything on his Instagram right now and considering selling my car. Well, he's starting to visit the state. So if any of your listeners are interested, he's starting to tour the United States more. He should be. Said Jim McCarthy. Great guy. What else in the, you know, that category of shoes, you know, somebody who's either making bespoke shoes, whether or not they kind of have that that range of MTO, MTM underneath them, just that you, who's working really appreciate. You mentioned Nicholas. I mentioned necklace. I do like Sebastian Terrick's work. It's sort of one of those things where I'm pretty happy with my relationship with Nicholas. I've been able to get him to make a normal pair of split toes. That was my first order to wear with Taylor Glow thing. I got him to make me a pair of split toes inspired by James Wesson's Demi Chasse. That turned out exactly the way I wanted. I got him to make me a pair of black side zip boots that were supposed to replace my side zip from Margella. He did that really, really well. And I'm currently having him make me a pair of tassel loafers. That seems to be the hardest to get right since those are slip on shoes and not something that you can kind of tie to the foot with laces. So I'm pretty happy with the range of styles that I've been able to get with them because I've changed the shape of the last with every order. So Sebastian Terrick is probably the only, he recently was in San Francisco and I normally would have, I tried to get a pair of black side zip from him years and years and years ago because I really like that kind of gritty, I don't know what you would call it, but he has kind of a gritty style. He can make you a pair of like normal West and shoes that you, you know, that you would order from any of the major West and firms. Yeah, that was like his day job for the longest time was. Yeah. Like just doing classic shoe bottoming. Right. But I really like his gritty style and I was originally trying to get a pair of black side zips from him. I wasn't able to get him to visit the US and he just recently visited the US and by that point I already had bought my side zips. But I like his work because he offers something distinctive. I also admire, I've heard really good things from friends about Katella who's run by Daniel Wigan. I don't have any experience buying from Daniel, but he strikes me. I sort of think that when you hire any of these people to do shoes or clothes or whatever, you know, you're hiring them based on their skill, expertise, experience, but also honesty and integrity because you're not going to be sitting by them the whole time. It's not like you're, you know, Patrick Swayze and Demi Moore and that goes scene where you're like holding, holding them from behind and making sure that they're, you know, doing things right. So you have to trust that they're going to do good work. Quite honestly, I bought from shoemakers that did awful work. It ends up being like a nightmare situation. And Daniel Wigan is from everything that I've heard, my interactions with him and then from everything I've heard from people in the industry, he is obsessive about getting things right. He's the kind of guy that's just like he will do it to the best of his abilities, even if it doesn't make any financial sense. And even if he doesn't like you as a customer, like he could have no incentive to get it right, but he will do it because he's just a kind, he's just the kind of guy that will like obsess to make sure that it's right. So I think it's good to work with someone like that because you're depending on them to honestly make the best that they can make and to not accept any compromise. So I think he's interesting and I think Amiko Masuda does really interesting work. Yeah. I would have gone with any of them, but I had just already chosen Nicholas Templeman. Some, I don't know, it's maybe been like, it's been over 10 years, maybe 11 or 12 years ago, somewhere around there. And I've been happy with all my orders. So I haven't felt the need to try anybody else. I mean, once you get that relationship, right, to get you, you know, and your feet, it's tough to say, let's start all over again. I, you know, I don't feel that way about tailors. I'm happy to always try new tailors. But for shoes, for some reason, like I just, you know, there's a certain, like Nicholas just knows at this point that I like really conservative, almond-shaped lass, he knows that I like split those. He just, it just works really well. So I haven't felt the need to try anybody else, except if, if I didn't already have my side zips, I would have ordered something from Sebastian when he visited. And then Seji is the only one that was like, like if I were to get a single monk from Nicholas, and I would have if Seji wasn't visiting the US, I would have literally just given him a photo of Seji shoes and say, can you make something that looks exactly like this? Because that's exactly in my head what I want to wear. But since he visited the US, I was like, okay, well, then I'll just get it from, so who else do I think does interesting work? You know, the hero, as we mentioned. Yeah, he makes a great split though too. Yeah. Fakuda, I think does really interesting work. The last are a little too shaped for something that I would want to wear, but like I'm very impressed by the shaping he puts into his shoes. Just so distinctive. Yeah, really, really distinctive. I think those are, and then the other ones is honestly like, since I feel pretty comfortable with where I am for dress shoes, you know, like I've been tempted, although I haven't really done it because as my wardrobe grows, I don't have the same temptation to get stuff as much. But I really like Brian, the boot makers work boots. Yeah. There was. And the other, the other one is, I'm going to butcher his name, but Felix, you're new. That's how I've been saying it in my head. J-O-U-A-N-N-E-A-W. He, he makes really cool bespoke work boots. I think those are really interesting and, and if he had, if he visited the US, I would be interested. And then the other one that I would love to order from, but there is a part of me, it's like, am I going through a phase right now, but Graham Ebner's bespoke cowboy boots, like that's something that I wouldn't order from Nicholas because it's so far a field from what he normally does. But I do wear cowboy boots quite a bit. I'm a little bit hesitant to buy bespoke pair because again, like I know if I buy a pair of tassel loafers or split toes from Nicholas, I know I'm going to wear those for a long time because those are things I've been wearing for like 20 years. But, you know, like bespoke cowboy boots are expensive. They're, they're not, I don't believe that they're cheap and they may be even more expensive than a pair of dress shoes from a West end shoemaker. And rightfully so, because he puts so much time not only into, you know, what you would normally consider just a bespoke order, but also the tops, the tops are so intricately decorated. But, you know, every time Graham Ebner posts a photo or a video of shoes that he had recently made, I just think, man, if money were absolutely no object and he were in front of me and I didn't have to consider at all my finances, I would absolutely order a pair of shoes. It's just at the moment, sometimes I think like, am I going to be wearing cowboy boots like 10 years from now? Am I just going through a cowboy phase or what? But I do wear a cowboy boots with some regularity, not ones as cool as what Graham makes, but, you know, when I see, when I see him post stuff, I just think they're so fun. And especially just the fact that you're getting them from one of the few makers, one of the, one of the people that still makes cowboy boots. Oh, yeah, I think that those, that's on my short list. So, Graham says it right on the t-shirt, which is all I can afford from him currently. Really nice, really expensive, and it's not messing around. But some of those pairs that he's made, like his production is like super low, right? Like six or seven, maybe eight pairs a year right now. One of them, we have old pug, I mean, not that old, but old-ish pug has with Graham where we have it on video too. So he really takes us through these big bend boots that are inspired by this kind of big bend national park feature in Texas. And I'm pretty sure them or the ones after them, like he took three months to make them. And like, and was working on them for three months. So, you know, when you kind of take the work days and divide the, the not cheap cost of that, everything starts to make a bit more sense. But yeah, I mean, everything that Graham's doing is incredible. I actually saw Peter from Wife at all the trade shows last week, and he was wearing his pair of Graham ebners. Oh, he is a pair of Graham ebners? Yep, like one of the early ones. Oh, man. Yeah, he was in early and God, they are phenomenal. They don't have as much top work. get some boots from Graham that aren't don't have all the inlay and overlay which is a lot of what he does he did on Peter's though while they're fairly straightforward you know for what cowboy boots can be the flowers on them that are on the tops like quite close to the top of the tops are like three dimensional right it's leather that's kind of oh yeah like the yellow the yellow three-dimensional folded flowers they does yeah yeah those are super cool like they're just I don't know they're stunners if you do you know make a mistake buying expensive cowboy boots and you just stop wearing cowboy boots altogether nothing looks better on the shelf then they're really beautiful like inlay overlay cowboy boots so not trying to push you in any directions also real quick back to Sebastian we have one too but I'd loved your episode with Sebastian on the die workwear podcast oh thank you it was fantastic everybody should listen and subscribe to the die workwear podcast you gotta pay for it and it's worth it it was great I mean all the episodes are great but I love that one and yeah Sebastian is he's just one of my favorite like people favorite rogues maybe in all the shoe making game he's I don't know he's just he's a fabulous guy to spend time with and has an exceptional beard yeah yeah I for me it's it's you know I'm fine with sticking with necklace for dress shoes or dress shoes adjacent and then so all the stuff that really interests me it's up for sedgies sedgies like again so so unique in that kind of space that I I really want to order pair of shoes from him especially because the MTO price is cheaper than spoke and he doesn't really well and so then the other ones that really interest me are mainly like workboot makers like Brian Felix I guess the cowboy boot is is you know kind of work is basically technically a workboot and so cramp cramp ebner and even Texas traditions I I would love you know to go go down there and order pair of shoes from them yeah I think those those are where a lot of my interest is is at the moment are you familiar with Nathan Floreshine no you should check him out he's nf bootmaker on instagram okay really interesting story he I remember getting this email from him like many years ago at this point and he's like hey my name is Nathan Floreshine yes I am of the Floreshine family he's like the fifth or sixth generation like Floreshine like direct descendant of old man Floreshine oh wow nobody in my family companies been like bought and sold and I think they have like some level of interest in it at this point but like nobody in my family and generations had like had their hands on a pair of shoes and so I kind of wanted to change that and um you know would love to chat and at this point I would say that he's probably you know for like a certain classification of enthusiasts who is into exactly what he's making because pattern wise he's expanded it a bit but he started out with just this service boot that in some ways you know to like the right eye is just perfect and he'll do some and has done a trunk show or two at this point and he's living in Chicago now and his stuff is just it's remarkable and so he just kept hammering away on that one service boot pattern that has again expanded a little bit and he makes some shoes but would just keep doing it and get better and better and better and better and better fit without being like a full troupe of spoke service for frankly like a really reasonable price I mean I think he started out there like eight on your bucks or something like that and now they're over a thousand but like closer to that than two thousand or maybe right in the middle he actually has a piece on our site too where he he breaks down everything that goes into that cost which was super helpful he like really just kind of opened up the books I guess and something I think everybody should read because it helps you understand that these expensive things are not actually massive money makers like Seji told me he's like we don't really make any money when you consider our overhead and materials and then just like time and being able to pay ourselves like more modestly than most people would think until a bespoke customer and lasts obviously included in that cost until a bespoke customer orders a second pair of bespoke shoes is when they start to actually like turn a profit on 45 hundred dollar and up bespoke shoes which was a pretty wild thing to hear yeah presuming they're using the same last for a second pair of shoes but yeah check out check out Nathan like it's it's you know kind of sleek ish like work boot approach and yeah I think it's it's hard to say that anybody's doing that exact kind of boot better and like is heavily works with the customers to do it to source just interesting leathers but like that's that's what you see that's the progression you see and you know my guess is he's if he's made the same you know style in the same leather twice or three times out of I think over a hundred pairs at this point like that would be it so like that that's where a lot of kind of creative growth goes but it's all in tandem with the customer what is the Instagram again and f like his initials bootmaker okay and it's really easy to see his work like he just for the most part he just post the work oh yeah yeah those look great yeah yeah those look great what else on like the boot side wait what are the cowboy boots that you said you you are wearing that don't cost more than a t-shirt my my are not you know like from they're not like super cool from I think JB Hill does really cool cowboy boots and obviously Rios Mercedes I was dipping my toes in cowboy boots so I've been wearing Tacovas which I think of as like the merement of cowboy boots or like I can't remember the price but they're like two hundred bucks or so so I have a pair of their oiled oiled leather ropers I can't remember the name of the model but that model I really like because they take on a patina really quickly which is good for desk jockey's like me and then I have a pair of their nor I don't remember the name of their models off the top my head but then I also have a norm I think it's called the cart right I have a pair of I believe their cart right boots but it's just like their normal standard cowboy boots that I also really enjoy I think the construction is pretty good especially for the money I have a pair of luchesy side zips I tried their cowboy boots and I didn't really like the leather that they used so I like luchesies a little bit better in suede Tacovas to me are a really good value especially if you like me are just kind of dipping your toes into that aesthetic what about like big big old work boots some Pacific Northwest boots some nicks or whites or francs or west goes or like are you into that kind of stuff I like them but I don't own any and I've never gotten into I know there's like a community of guys who are like super super into them they're listening but no I don't I don't have anything from them and I have a pair of one or two pair of vibers I haven't worn them in a while I bought a pair of vibers and I was like who those are my work boots and I'm done so that's the idea yeah those are basically it so how old are the vibers I don't know like it's crazy to think it's 2025 at the moment can't be I mean over 10 years so oh okay so they're like hold from the day yeah because they've a lot has changed and like get listeners of this and and people in our community you know we in our discord we have like a referred to as like a containment zone called viberg talking so like the viberg talking you know positive negative or otherwise is restricted to there somewhat and yeah there's a lot of talk like whatever you have I'm sure that people would be quite high on those because yeah they just in terms of everything that they do like breads change the brand and the manufacturing even like the construction like everything used to be stitched down and now there's a lot of well construction that is just there was something special about vibergs from from that era for a lot of people so don't get rid of them yeah I have those stitched down ones I'm not I'm not the kind of guy to care if they're like stitch down or could you're wilted or anything like that but I do have the stitched down ones I don't know I think the good you're wilted ones are fine I know that's like sacrilegious and some people well I think they just look different but visually like there is something of like those high SPI old vibergs that a lot of brands try to duplicate over the years and still are and like nobody ever got it except viberg from the era where you got those boots so yeah big thick heavy heel counters that just really work you over yeah yeah they're cool because they were like legitimately just the work boots that they were making except that he started making them to obviously different patterns and stylistically, quite different from like a big tall logging boot, but like the guts and the manufacturing was exactly the same, which I love. I love a boot company that makes shoes. That's kind of what I like to wear. - Yeah. Yeah, I find they go, the, the, the fibers I have, I find they go with the wide range of styles. Pretty easy, I'm obviously not tailoring, but like pretty easy to pair with like any kind of workwear, but even stretches into like the kind of streetwear that you'd find at like Haven and Canada. So, I think they're a useful shoe. - Quite useful. What about engineer boots? Where are you at on engineer boots? - I bought two pairs way, way back in the day. Not two back, I don't even know. I've totally lost track of time, but I have two pairs of engineer boots. Mr. Freedoms, I believe they called them the road champs, and then. - Oh, the road champs. - Yeah, the pair of road champs. And I have a pair of John Loffgrens, which do not fit me very well, but I have a pair of John Loffgren engineer boots. And over time, I just don't wear them very much because my, my casual wear, it's sort of like what the boat shoes is just like it's not, it's not like Inspiration LA and like super, like super duper rugged. So, I wear, you know, like I don't feel like I wear the kind of clothes necessary to wear a pair of engineer boots. But I did like engineer boots for a while, and I still like engineer boots. I just don't wear mine very often, but I really like the way that Mr. Freedoms constructs his. There was like a thing like way back in the day where he and I butted heads a little bit. So it makes, like I have a bunch of Mr. Freedoms stuff that I bought at full price. I don't do freebies, and I wasn't like, you know, getting like friends and friends and family discounts or whatever, I bought them at full price, or I bought them at the same sales that people would, you know, like, had access to. But then like after the, we had like a little bit of a dust up, it just kind of like, I don't know, it just kind of made it, I don't get as much joy out of wearing them. But in terms of like style and construction, I really like that he used a T-core leather for his road champs. I think that makes the engineer look even cooler over time. I have a pair of persimmon dyed Capitol side-sips that I really love that have a similar effect to that kind of T-core leather. I really, really like those. But if someone was wearing going to get engineer boots, I would say I would consider whether or not your style is like that kind of like super rugged fedora lounge, inspiration LA kind of aesthetic. I found the John Laufgrens a little bit hard to fit because he uses an extremely shaped and rounded heel counter. So since they're slip on shoes, essentially, or slip on boots, and you can't really tie them onto your foot, you have to make sure that the heel cup is like gripping you in some way and mine just don't grip as much as I'd want them to. But his were very beloved among guys who like engineer boots for a while. I think they're still nice boots. I would just encourage you, if you're buying John Laufgrens engineer boots, buy them from a shop that takes easy returns and pay attention to whether or not the heel cup is gripping you as it should. - It's hard to argue or let's say one can argue that there's nothing cooler than a old beat up pair of engineer boots in terms of boots like they look so cool. But I was afraid of them like personally. It's like how do I do this? What do I wear with them? And then wore them basically every day for like a month and kept a diary of this like descent into engineer boot madness and published it and really ended up loving them. And like I actually found that they were easier to wear like not like hot hot summer, but like jeans and a t-shirt. 'Cause you can just wear them with some salvage denim and a t-shirt, white t-shirt and like you look cool. And then as soon as it starts to get a little cooler, like I'm pretty sure that I have like a cowboy type shirt with some pearl buttons like in my closet somewhere and you're like looking to dig that out. So you can like more effectively wear those engineer boots. People who do it, like I don't wear leather jackets. I don't, it's just not me. But yeah, when they make them work, like gods are good. I'm gonna try and wear some engineers soon. It's been a minute. What about monkey boots or lace the toe boots in general, which are favorite of mine? - I have a pair of monkey boots. I'm now sounding like a shoe guy, but they're great. But yeah, I bought those way, way, way, way. Those are definitely like near 20 years old. And never wore them. They're just, they're just a little too, too out there. - What are they? - I think mine are from Grandson or something. They're way in the back of the closet. I've not seen the light of day. - Oh, so like a British style monkey boot, yeah. - Yeah. It's a little mod situation. - Yeah, I sort of think that you have to be, like just figure out what clothes you wear most. And then to state the obvious, just figure out what clothes you wear most, what's the style you wanna create, and then buy a shoe that works with that. Like the kind of monkey boot, donkey jacket. I think for that monkey, at least the ones that I have, I think you need like the British donkey jacket. You need like, it has to be like a very specific kind of, like British workwear, kind of outfit that I think looks good with that. And I just don't really wear stuff like that. Those never really got anywhere. The ones that I recently bought, I don't know the name. I don't know, I pronounced the name of the company, but D-I-E-M-M-E-D-M-E, D-M-A, that D-M-A, Rocha, D-M-A, that Rocha, that sport, something that they made on a year or two ago, in a very hairy swayed. I've been wearing those a lot, I like those. I know they're not like super like niche cool, kind of like high end or anything, but I do really like blunt stones, still like blunt stones. And I wear those ropers and I wear my capital, persimmon dyed, sides of boots. Yeah, and I still really like sides of boots. I think those work better with contemporary casual wear. I'm trying to think of what are the boots that I wear. I can't get there on side zips. I think I have the wrong clothes, maybe. Or I'm just not cool enough. No, no. For example, like Tacovas makes a side zip that I think can be worn with Western wear. Luchese also does their Jonah boot, which I think works with Western wear. But I generally think of side zips as something that you wear with like Lamar and Margella and like very contemporary, kind of like fashion brands. I really like how they look in those outfits. But the problem is always finding a side zip that doesn't, like I think once you understand anything about shoes, you're gonna be disappointed with a lot of side zips 'cause a lot of fashion brand side zips are not made very well. So I have Margella side zips. I like the design, but the build quality is like, man, couldn't you have like just put in a little bit more effort for these like boots that you charged a ton of money for? Oh, it's not there. Le Boute Gardin, it's this French boot making company. They make side zips from full green leather that I think are really well made. If I was buying side zips again, I would shop there. I think if you like that kind of contemporary casual or style side zips work really well. Those are basically the boots that I wear most often. You know, I've purchased like Edward Green Gowais and I just never really wear them. What last, do you know? Trying to think, jogging my memory. I think mine are on the 202, so that's the round, that they have the 606, which is the slightly chisel toe and then they have the 202, which is the round toe and they have the 82 and the triple eight. And those, the 82 and the triple eight are a little bit too sleek for my taste. So I mainly stick to the 202 and 606. And I believe my Gowais were on the 22, but they're a little too conservative classic menswear for me for casual wear. I just don't wear a lot of classic casual wear. So I see myself as very much a form guy. So like on style form, it's split between CM, which is classic menswear used to be called MC mens clothing and then SWD. And I think of the Gowais as a very MC, CM kind of boot. The casual wear, it's for the outfits, for the casual wear, for the guy who normally wear suits and sport coats, like barber jackets and stuff. And I just don't really wear that stuff very much. They did make a pair of, they used to do Gowais on a really heavy last way back in the day that we're shearing lined. I really like those with Nigel K born, which is a casual brand that I really like. I don't think they make them anymore, but it's on a defunct last, that's a number I can't remember anymore. But on a much more casual last, I think those look really good with workwear. The Nigel boots, I'm not sure, I'm gonna have to look those up with the shearing lined. I don't remember we're seeing those, but I think they'll still do them on, I believe the 64 last. I think it's the six, is that the really rounded one? It's super round compared to the other last that they're doing stuff on. [BLANK_AUDIO] or Edward Green, it's like, you make shoes like this, you use the last leg there? - Yeah, like you wouldn't even expect it in the line and it completely changes the boot, completely changes it. - I think that's the one that I have. It's a Sheerling line, a Galway on the '64, and I find that goes really well with like a pair of jeans and a Nigel K-borne jacket. I think if you like engineered garments and Nigel K-borne and you know like chorecoats and trucker jackets, like that kind of world of workwear, where it's not super repro, then that kind of boot works really well. But Edward Green, I don't think they make those anymore. Maybe you could special order it, but that would get to a price where I sort of feel like, I bought mine off eBay, they were like super old. They were made back on the day and I just bought them off some guy who just didn't wear them very much. So maybe scour eBay, but if you wanted that kind of boot, I would just, there are so many makers now that offer good things that you can wear with those outfits. I don't think you have to go for that '64 evergreen Galway. - Yeah, those are basically the boots I mainly wear. Yeah, I would say those. - That was really good. Those were all boots that we discussed. Which was the goal. - I don't know, I mean look, I'm enjoying the hell out of this, Derek, is there anything else that we miss? Do you own a pair of Crocs? - I don't own a pair of Crocs. Michael Anton, now heading one of the departments under the Trump administration, but former style forum Titan, he wrote the book The Suit and went under the name Anton on style forum. He owns a pair of Crocs. That was like a famous thing back in the day because he used to take photos in his bathroom and someone spotted a pair of gray Crocs. And this was like, 2000. - Yeah, I don't like. - 2008. He posted this photo in like 2006 or 2008. So way before Crocs were accepted in Mensavers' service. And he had a pair of gray Crocs in the background, which I thought was really funny. 'Cause if people know, he was very well known on the forum for having super conservative Mensavers' taste. That was like his thing on the forum, it's like trying and I think a good force on forums of pulling back the reins and trying to get people to not do hashtag Mensavers into his taste of the love to conserve for me, but I think it is good to have someone on the forum be like to have that countervailing force. But super weird for him to have a pair of Crocs. That's my one Croc story. But I don't, I don't personally don't own a pair of Crocs. I've never tried them, but I've heard they're super comfortable. Yeah, I don't even know if I agree with that. I have some that I use when I'm like fishing on a tiny little boat that you have to like shove into the water up to your knees kind of thing. So it's like, that's when you wear the Crocs. And no, they're not comfortable. Oh, really? They have like all those little nubs. I don't know, they're squishy in the Crocs and socks. Like people do, you know? It's like tell Joe's in the emergency room recently, and, you know, they're wearing the right comfortable footwear. I'm sure there's also trend driven stuff happening with hospitals and other people who are on their feet all day long. But now I don't find them to be comfortable, not just because like they're Crocs. And so you say that they're not uncomfortable, but a lot of other stuff is better. I think that's overbuilt in terms of like I wear Crocs reasoning, personally. But they do have holes in them and the water goes out of them. I'm not snobbish about it. I don't think people are bad for wearing Crocs or anything, but the only thing in my wardrobe would go with Crocs. So I have no, that's not my shopping list. The other boots, which is a company that I know you've worked with is Russell Mockison. I got a pair of boots from them made from a photo that I found free and easy did a special Ralph Lauren issue. And they showed a pair of boots that Ralph Lauren released in the '90s made by Russell Mockison. I sent them a photo and I was like, can you recreate this exact boot? And they did and they're great and I like them. I like those. They do take a bit to lace up. And the other thing is someone made a pair of shepherd supposedly, who knows. But supposedly, this style of boot was inspired by what shepherds in like Spain or something used to wear. Someone made a pair of boots years ago inspired by that. But there's such a pain to lace up by the light that style. And I've always wanted a pair of Guidi. I don't know if that's how you pronounce it, Guidi boots. They did a collaboration with Casey Casey. The problem is that they're like so expensive. I already have boots that I wear and I'm happy with. So then when I see that price, I'm just thinking like, man, if I didn't have anything, I feel more comfortable spending that, but like if I already have boots that I am happy with, like there's no, I don't feel the need to like constantly buy more. But the Casey Casey collab with Guidi was like, it was tempting. I really like the way their boots look. And I think, you know, like Guidi's boots are all for that market that's wearing like Carol Christian Powell and Rick Owens, like Andy and like this kind of avant-garde stuff, which I like as an aesthetic, but is not in my wardrobe at all. Like I don't wear any of that stuff. But the Casey Casey collab was something that I could see working with a pair of jeans and a trucker jacket, like just super normal workwear. That was on my shopping list for a while. But you know, Guidi boots are super expensive and rightfully so because of the amount of work that they put into them. But the price was like, maybe hesitate. - I think that's reasonable. But yeah, I think Guidi's cool. Like that kind of stuff, my God. Like the CCP boots, like some of them are so cool. The tornadoes or obviously the ones that, you know, they're like fucking terminator. They're incredible. I've got to see a bunch of them, like in person, I'm gonna try some on. They're not me. I certainly don't have like the clothes to back them up. And I think that's where some of the Guidi stuff is, can tilt in that direction. There's incredible things that they do, you know, with the leather kind of bunching up and whatever and like they're making the leather. And then, you know, from what I've seen and handled and just heard from people, like the Guidi construction is legit a lot of these fashion boots. Like they're just not, right? They look good. - Yeah. - People like them, right? Whether they kind of have different reference points or not, like, or they just spend a ton of money on them and so want to like them, like people really like them. But like it's compared to a lot of this stuff. It's just not, but the Guidi stuff generally is like really, it's like all thoughtful and very well done. It's still quite expensive. But yeah, then some of it's like a little bit more straightforward, but like the leather is, it's kind of unmatched. There was, Viber did a little bit, like limited runs of just like, I think they were usually service boots. Maybe some shoes in some Guidi letters. They're phenomenal. Anything else? - Yeah, I don't know. We can stop. - Yeah, I think we've covered it. Fabulous, this was incredibly enjoyable there. - Yeah. - Yeah, I think we literally covered like the entire footwear, welted and other universe right there. That was great. - Yeah, thank you for having me on, I appreciate it. - Anytime, Derek guy, appreciate you. Check out Derek kind of everywhere. His die-workwear blog, the die-workwear podcast on Blamo. Put this on, New York Times, Washington Post, Wall Street Journal, I think, Twitter. Thanks a ton, talk to you man. - Thank you. (upbeat music) - Hey, it's Ben again. Thanks for listening. Hope you dug this one. Here's the part where I remind you that this shoe cast wouldn't exist without the support of our stitch down premium subscribers. So if you're enjoying it, I'd love if you stop by stitchdown.com to learn more about the membership and the community we're building online in an actual real people life. For over half a decade now, we're starting to tape a few subscribers-only bonus episodes, which should be quite different and pretty darn fun. So definitely stay tuned for those. I think you'll like them. That's it for this week. Take care of your shoes. We'll see you next time.

Podcast Summary

Key Points:

  1. Stitchdown Expo 2026 in Chicago will feature over 50 global footwear makers, tanneries, and live shoemaking demonstrations.
  2. Attendees can try on finished shoes and receive expert sizing, ensuring better fit and comfort.
  3. The event partners with Superdrunk to showcase high-end dressy footwear and industry culture.
  4. Derek Guy, a renowned menswear writer and shoe enthusiast, shares insights on comfort, craftsmanship, and shoe styles like moccasins and split toes.
  5. Handcrafted moccasins, such as Townview and Arrow, are praised for their comfort and traditional craftsmanship, now at risk due to small-scale operations.
  6. Derek highlights the importance of trusting skilled shoemakers and emphasizes personal fit over trends.
  7. He recommends buying from small, artisanal brands to support traditional craftsmanship and avoid supply chain decline.
  8. Shoe sizing and fit vary significantly, especially with French brands, making in-person fitting and returns essential for success.

Summary:

Stitchdown Expo 2026 in Chicago will offer a rare, hands-on experience with over 50 global footwear makers, featuring live shoemaking, expert sizing, and the chance to try on finished shoes. The event will also partner with Superdrunk to highlight premium dress footwear and community culture. In a deep-dive conversation with menswear writer Derek Guy, the focus shifts to the value of craftsmanship—particularly in hand-sewn moccasins like Townview and Arrow—whose traditional, small-scale production is vulnerable to collapse.

Derek advocates for mindful consumption, urging fans to buy now before these artisanal traditions vanish. He emphasizes that comfort and fit matter more than style, citing the unique footbed and moccasin construction that adapts to the wearer’s shape. While brands like Jam Weston and Paraboot are praised for quality, their sizing can be unpredictable, especially in European markets.

Derek highlights the importance of in-person fitting and trusted makers, such as Nicholas Templeman and Seji McCarthy, who offer made-to-order services with attention to detail. He also champions bespoke workwear and styles like split toes and tassel loafers, which reflect a more authentic, timeless aesthetic. Ultimately, the conversation underscores a deep appreciation for craftsmanship, tradition, and the human element in shoe-making—a response to the decline of artisanal industries and a call to support sustainable, high-quality footwear.

FAQs

Stitchdown Expo 2026 will take place in Chicago on November 6th and 7th, 2026.

Attendees can meet the makers behind shoe brands, watch live shoemaking and repair demonstrations, and try on finished shoes for expert sizing.

Yes, Stitchdown is teaming up with the Superdrunk team to showcase high-end dressy footwear and related products.

The expo features 50+ quality footwear makers and tanneries, offering a wide range of handmade shoes, boots, and accessories from around the world.

Yes, attendees can try on finished shoes and receive expert sizing advice to ensure a proper fit.

Moccasin construction involves a wrap-around vamp and a soft sole that molds to the foot, offering excellent comfort and a unique fit over time.

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