In this bonus episode, host Sherry Brasier interviews her client Debbie Oltson about her style journey. Debbie initially wore "safe" and predictable clothing—mostly neutrals like black and white—because she didn't know how to stand out or what colors suited her. She felt stuck and lacked confidence in her wardrobe choices, often buying similar items without purpose. Through working with Sherry, Debbie learned to shop with clarity, focusing on pieces that align with her personal style and can be mixed into multiple outfits. Key tools included outfit challenges and style boards, which helped her experiment with new combinations, discover items already in her closet, and push her limits—like wearing a blouse she'd never tried, which earned compliments. Debbie now feels more familiar with her wardrobe, avoids aimless purchases, and saves both money and mental energy. This newfound confidence extends beyond clothing, positively impacting her business by making her feel more prepared to lead and represent her brand. Sherry emphasizes that style transformation isn't difficult—it's just new—and that learning core principles turns the closet from a stressful place into a creative one. Debbie's advice to others is to take the first step, as investing in yourself leads to greater self-worth, long-term savings, and overall improvement in life and work. The episode highlights three main takeaways: confidence starts in the closet, shopping with clarity saves resources, and style is learnable and fun.
[Music] Did you know that you can have unshakable self-confidence? I'm Sherry Brasier. I'm an advanced certified style coach, personal wardrobe stylist, and seasoned hair stylist. I'm on a mission to teach women everywhere, to see their true value and create self-confidence on the inside, and then help you dress that way on the outside. Women, just like you, are craving strategies to dress your body shape stylishly, tools you can use to help you love yourself and process disappointment and overwhelm, all while still looking put together when you leave the house. If you're ready to figure out your personal style, and learn the tools to help you build and create more self-confidence, then you are in the right place. Let's get started. Hello, my friend. Welcome to this bonus episode with my client Debbie Oltson. In this episode, I sit down with Debbie and reflect on her style journey, and it is so good. You are not going to want to miss it. From feeling stuck and safe and predictable clothing to confidently putting together, herself with color, creativity, and purpose, Debbie shares what changed everything for her. If you've ever stood in your closet thinking I have nothing to wear, or left the store overwhelmed by choices, Debbie's story will feel like a deep exhale and a fresh perspective. In this episode, I'm going to give you three takeaways of what happened with Debbie, and what is happening currently with Debbie because she's still working with me. She's still one of my clients. The first thing that we talk about is that confidence starts in your closet. Debbie shares how dressing with intention helps her feel prepared to lead in her business and more confidently in her life overall. When you fill pull together, it shows in your posture, in your energy, and in your impact. So number two is shopping with clarity, saves time, money, and mental energy. Who doesn't want that? Debbie now shops with purpose, choosing items that align with her style, and actually works with what she's already got in her closet. No more aimless buying, or that pile of cute but never worn pieces. How many of you have those in your closet? I know you do. And the third thing that we talk about is it's not hard, it's just new. So what surprised Debbie the most was how simple and fun it actually is to get dressed, once you learn a few core principles. From the style boards, in the outfit challenge, plus the style boards in the membership that she's in, Debbie shares how these tools have helped her turn her closet into a confident place instead of a stressful one. She actually loves going in her closet and getting dressed every day. And she is putting together some of the funnest outfits that are just right in her closet. If you've been thinking about finding your style, or you've been wondering what it's like to work with me, this episode will give you a front row seat. Debbie's honest reflections will inspire you. They will encourage you and they will help you to show up feeling amazing in your clothes. And it's not just about buying more, it's about knowing more. So grab your earbuds, hit play, and come hang out with us. You're going to love this conversation. Hi Debbie, thanks for coming and visiting with me today. It is my pleasure. Yeah, you're such a, you're so cute. So we're just going to reflect on how far you've come in your journey. And we'll just talk about style and clothes and all the things you want to talk about. But I just appreciate you coming on and doing this little interview for me. So I appreciate it. My pleasure. Okay, so tell me where you were style wise. And in your wardrobe before we met before we started working together. I wore the same stuff all of the time. I wore safe things that I felt. I don't want to say comfortable, but comfortable in. And that doesn't make comfortable as in they were my comfortable clothes. They were the things that I felt. I just wore the same stuff all the time and it was boring. You know, same old thing, nothing exciting or new. Yeah, when you say you were safe clothes, what do you think? What does that mean? I wore all of the same colors, all of the same types of shirts or pants or shoes. Okay. Very, yeah, very predictable. Okay. Okay. All right. So did you, did you feel like you just didn't want to, or you didn't know how to stand out? Greg, I didn't know how. Did you want to? Yes. Okay. You wanted to stand out in your business or just in life in general. It life in general in all ways. Yep. Mm-hmm. And just didn't know how. This didn't know how. Okay. Yeah. Yeah. You look at other people and you go, oh, that's cute. But then you don't know how to implement something like that in your own. Mm-hmm. With yourself for yourself. Yeah. Right. I get it. Yeah. So were you, were you having any particular challenges? As far as like what you had in your closet or what you were wanting to put in your closet? Tell me about the challenges of not knowing what to add to your closet. Definitely not knowing what to add. I have learned that I buy a lot of neutrals, you know, a lot of black and white in my closet. So it's been fun to start to add patterns and colors and be aware that when I'm shopping, you know, I don't need another black shirt. It would be fun to buy a green one or a pink one or, you know, something like that. So that's been really fun. And to just be aware of don't buy another pair of blue jeans, you can, you know, go outside the box a little bit and maybe try on some gray ones or some brown ones. That kind of thing has been really fun. So do you think that adding color that your challenges of adding color, you know, whether it's a gray pair of pants or whether it's a pink shirt. Or whatever was because you didn't know what your colors were. That and I didn't know what colors I might want to buy. It's always safe to buy the black or the neutral, but adding color in is just, yeah, I just didn't know what to get. Okay. What's changed now? How do you know now? Specifically in the challenge where you provide us with an outfit to try and copy. That's helped me go into my closet and go, look, I do have a pink shirt or I really like that shirt. I'm going to go shop for it and try some of those things on. I've put together things that I wouldn't have put together in the past. So going into my closet, looking for what's already in there has been really fun. And then with the style boards that you provide being able to go, I really like that outfit. I'm going to try that has been fun as well. Do you think that the challenge has added a measure of like, oh, those two things go together. I have both of those things. I wouldn't have known those two things go together. Is that part of it too? Yes, absolutely. And the other part of it is seeing what the other women put on and the things that they decide to wear and me going, oh, that's really cute. I have something really similar to that that I can try. So not only what you're providing, but also what the group's providing as well. Yeah. One of the other girls in the challenge said that this week, like, I didn't realize that I have so many more outfits I can create because of all of the outfits that you guys are all putting together, which I thought was really. A benefit that I hadn't really considered myself. Yeah, that's been really fun. Yeah, that that would be something that would be useful, right? What would you like, how would you describe the way that you're thinking about yourself and feeling about yourself and your style before we be on working together? What was the the verbiage and the thoughts that you and your beliefs? Before basic, just pretty basic. I didn't even wear a belt, you know, I black shoes all the time, just very, very basic. And I don't feel like that now at all. It's interesting to push myself a little bit more and when I find when I push myself and do where the jacket that I might not have worn before, I'll get compliments where people will, you know, oh my gosh, look at you in that jacket or different things like that. So I feel like I've just leveled up a little bit with, you know, color or adding a jacket or putting on a belt or putting on a collar, you know, those kinds of things that just add a little bit of. That just they just boost you up. They just make you feel good that you're, you know, taking that extra step. Make sure you feel pulled together. That's a lot of the, that's what people tell me like my clients will tell me that they don't feel pulled together or they. They don't feel like they're complete.
And now just adding a few little things like a belt or, you know, a jacket or some jewelry or whatever just makes it feel more complete. Mm-hmm. Yeah. I'm also finding that when I now when I shop, I have a better idea of what I'm looking for. So I'll see something to go, that's cute and then I can go, but I don't really need something like that. I need something like this. Mm-hmm. I'm more aware of what I need, what I am out shopping. Mm-hmm. Yeah, and I think that's huge. I was on another call this morning and she was asking me a question about about a something that I had done and she said, "Well, is it worth it?" Right? Like, was it worth it? And I said, "That's kind of a loaded question because what I thought that I was going to get, I didn't get, but what I did get was I know exactly what I'm looking for and I know exactly what I'm not." Mm-hmm. So even though I went into that, you know, partnership or that collaboration thinking that I was going to create this XYZ and that didn't happen and that was kind of, you know, disappointing on my end. Like I was kind of disappointed about that. Right. But what I gained, I didn't realize I was going to gain, which was I know exactly what I'm not going to do. Right. And I hope that that's what I help create for you is knowing when you go into the store, when you see something, you know you like it and you know if it's something that is going to be in your closet. If you can utilize it in your closet. Well, and I also think about now, yes, that definitely. And I also think about now, I'm way more aware of, okay, I have these shoes. So are, do the shoes I have, are they going to work with these pants or the stress or, you know, whatever. So instead of thinking, not the cute pair of slacks, I'm going to buy those, I think about what I've got that I can incorporate with them or if I'm going to, you know, I know if I buy these, I'm going to have to buy something to go with them. Mm-hmm. So it's, I mean, I've gotten familiar with my closet now. Yeah. And how does that feel? Good. It's really nice. And I mentioned this in the challenge yesterday, the day before when I said, I grabbed a shirt that I wear all the time and I went, nope. This is a challenge. You're supposed to be, you know, pushing yourself a little bit and I went back in and found something else. And I've, I've never worn that blouse and I put it on and I got complimented on it. And it was fun and so I was proud of myself for like, you know, pushing my limit a little bit. Yeah. Yeah. So we've talked about the challenge a couple of times. For anyone who doesn't know what the challenge is, I want you to describe what it is that we do on the challenge. The challenge is so fun and I will admit that that's the way I did, I did the last one and I participated in this one. And initially I didn't really know what to expect. But it's really fun to wait for your email at 6 p.m. every night and there's an outfit for the next day. And the challenge is you go into your closet and you try to, you know, put this outfit together, you know, see how you do that kind of thing. Of course, you might not have in your closet those items, but then you still can try to, you know, put something similar together, those kinds of things. So it's really fun to participate in that with everyone. And also it's helped me to notice where I do have gaps in my closet. So when I go shopping, I can say, oh, I don't have this, you know, type of blouse that can be, you know, can be utilized in all these different ways. Mm hmm. Which I think that. Yeah. Keeping me how to use different clothes in different ways. Mm hmm. I always tell people that if they're going to purchase something, it has to be utilized in your closet three different ways. So we have to have three outfits that we can put together with that one pair of pants or with the one shirt or the pair of shoes or whatever. And then also if there, if this is a special occasion outfit, then that's different. If you're only going to wear it that one time and you're good with that and you have, you know the reasons you're doing it and you like the reasons you're doing it and, you know, all the things that's fine, but in your everyday wardrobe, I want you to be able to have three different outfits that you can put together with one shirt because no one really, no one wants to buy something and then only be able to wear it once the same outfit each time. And it's just in your closet and you can only wear it that one time. I think that feels really restrictive to most people. Yeah. Well, that ends up being the stuff that you never wear because you're only wearing it. Sometimes. So that's, I love that idea. I don't know if I ever heard you say that, but I, that's another little key element that I'm going to carry along with me now. Yeah. And I think that's one of the things, one of my main reasons for doing the outfit challenge was to show you multiple items that are that we're going to be using in a two week span of time and you're going to have totally different outfits with those items. So because everyone wants a capsule wardrobe, they like the idea of having a capsule wardrobe. Really what you're saying when you say I want a capsule wardrobe is I want to be able to wear my clothes more than just with one thing. Right. And you want to have clothes that you wear. You don't like it's not that fun to have 100 shirts in your closet and you wear 20 of them, which I think is most people, most people. And I love that you that you mentioned that you've gotten more familiar with your closet and that you, you're more familiar with what's in there and you're utilizing more of your clothes because there's, there is data that we as women, 80% of the time wear 20% of our closet. Yes. And I believe that 100%. And that's the other thing. I'm getting more familiar with the types of clothes that I'm worried and what I find that I feel good in. And so when I'm shopping, I'll see something and go. I know that I won't wear that because it's that kind of shirt or it's that kind of, you know, the cut or whatever. And so then I don't, I'm not purchasing things that I'm not wearing. Mm hmm. Which is saving you a tons of money. Mm hmm. First of all, saving tons of money. But what I care about even more than that is the mental brain power that you are now saving because you don't, you're not going into, I don't have anything to wear. I'm at the store and I don't know what to buy and it does this look good on me. Does that look good on me? And this doesn't work and that doesn't work. And I don't know why in like all of the things that people hate about the dressing room. Right. It's not happening. Right. Because you're like, yeah, that's not going to work. And these are the reasons why it's the garment. It's not me because mostly it comes back to, I just need to lose weight. And then I could wear that shirt. And now you know that that shirt, no matter how much you weigh, doesn't work on your body. Right. It doesn't work on your body. It doesn't work with your wardrobe, it doesn't work with your style, whatever. Now you know that. It's not your body. Mm hmm. And I think that is like worth all the money in the world. I agree. Yep. Yeah. And it's been fun. It's really fun. There's so many people that hate getting dressed in the morning. It's like they're worst part of the day. And I love when you guys, I will see you out in the, out in the town, you know, out in the world. And you're having fun getting dressed because I think it's fun to get dressed. And I want everyone to think it's fun to get dressed. And so I love that. So talk to me about your business. Do you feel like this has had any effect on your business? Absolutely. I feel like I'm more confident when I'm, when I feel like I'm put together. And so that in turn shows up in my business when I'm representing the business, when I'm working, all of those things. So it's definitely had an effect that way. Mm hmm. Do you feel like you've gotten more clients, more business? Do you feel like your revenue or your, your business has grown? We're definitely busier. That's so that's good, right? I think that for me specifically, it's just made me feel more confident going into the world saying this is what I do. And you know, when you're confident, you hold yourself differently and you speak differently and you, you just feel differently. And so I imagine that that does trickle down and have an effect on your business, your relationships, all of those things. I think that one of the things that you had said that really was a highlight for me in my mind was when you said that when you're dressed better, you feel like you're more prepared to lead. Mm hmm. And I thought that was me. Yeah, that's a huge, because as a business owner, whether you are in business by yourself or whether you have a team or whatever, if you feel like you're confident to lead, that is huge. Mm hmm. That's huge. Yeah, that makes a big difference for sure. Yeah. Yeah. So I love that. So what made you decide that now is the time for you to work with me and to figure out your style? Well one is knowing that you're there, right? You, I think that you can recognize that maybe you need a little assistance.
in that area, but you don't know where to go. So one is having found you. Two is being brave and doing it. I think that, you know, when it's like a weight loss challenge, I got to lose five pounds before I go on to the weight loss challenge. No, that's not the point. You know, we're going to, we want to teach you things. And so, so you can be where you want to be. So one is being brave enough to do it. And I think lastly, it is because I'm a fairly new business owner. And I do want to feel confident and look good and put together. And when you show up dressed well, not meaning like, you know, in $500 clothing, but dressed in a way that you feel good and comfortable and, you know, like a leader, that makes a big difference. So it's just, you know, having that desire to to spend my money better and to, to buy things that are, you know, make me feel good about myself. Mm-hmm. Did you ever have an issue whether consciously or not that you were worth spending money on and that it was like, did you ever have any thoughts of, oh, I can't do that because I need the money, other places or I got to spend it on this or that or the other. And, and all of that just leans into, I'm not good enough. I'm not worthy enough. I think what's upon a time I would have, thankfully, I've gotten to a point in my life where that's, I don't feel like that's so much of an issue for me anymore, but there certainly would have been a time when yeah, I would have felt that way. Mm-hmm. Well, if there's someone that's, that's feeling like that, what would you offer to them? You'll feel better about yourself if you take the plunge and that's going to make you feel more confidence. It's going to, you know, it's just going to make you feel better overall, which then is going to help you level up to the point where you do feel worth it. And back to knowing what to shop for and what you feel good in, you really, you'll save money in the long run. So it's kind of a win-win, not kind of, it is a win-win. Yeah, well, it was one of the things that was the most surprising. What was one of the things that you weren't expecting that happened that you were like, oh my gosh, I was not expecting that. It's really easy. It's very simple. It's not hard. I love it. That's my favorite. Yeah. That's not hard. It's just very simple and it's fun. Yeah. It's interesting that we make things in our head. They just, they just sound so difficult and hard and unachievable. And, you know, there's so many reasons why this isn't going to work for me or it's not going to happen or I won't be able to do it or, you know, she can do it, but I can't. Mm-hmm. But you've had to read this. It was easy. Yeah. It was easy. You came over. We looked in my closet. We did some stuff. I had a great time. You know, it was really fun. I learned some things and then just kept going. So yeah, it's been really fun. Yeah, I think that's one of the, that's one of the things I like to go ahead. Yeah, it's not intimidating. You don't feel uncomfortable. You don't feel silly or weird or any of those things. It's great. It's fun. Good. I'm glad. I'm glad that that's the experience that you're having because that's the experience that I want people to have. It is easy. It really is. It, there's really only a few things that once you understand, it just opens up so many more things that you're like, oh my gosh. If this, then that and that and that too, there's one thing that changes. You're like, oh my gosh, that affects so many other things. I can do so many other things at no idea. That's what people will say. Yeah, I agree. Yeah, how much easier? Awesome. Well, if there's somebody that is wondering, should I work with Sherry? Should I join the membership? What has been your favorite thing about the membership in general? I like having access to your class. That's been really fun and that's taught me lots of things. I think I shared with you that you have us in the class. You have us put together the likes and dislikes of the style board. I had done that and I was looking at the clothes that I liked and I went, I have everything in my closet that's that outfit. I pulled it out and I've worn it a number of times and I would have never put that outfit together. Had we not done that exercise? So just having access to that and just all the things that you have in there, it's just it's great. I'm just whittling my way through it and every time I do one of the little modules, I learn something new and I like I'm just having a great time. Yeah, I'm glad. It's fun. Yeah, I'm glad. And you're just there. You're just there with us every day and so that's really fun. Yeah, I can just go with you on your walks and in your car. Yeah, exactly. When you're doing a car, yeah, just get a little sherry on your shoulder. It's kind of fun. Oh, yeah, I love that. That's so fun. That's that's that's so good. Well, if there is anything else we haven't talked about that you would love to touch on, that you just want to make sure that everybody that's listening knows. It's just a really good time and you're going to make friends virtually and so yeah, I'm just having a blast. So I would just hands down be like don't hesitate. Just jump in because you're going to love it. Awesome. Thank you. I appreciate it. And I appreciate you being in the group. I appreciate you being in the membership and the way that you present yourself and the advice that you give and the accolades and the just like the encouragement and you're so compassionate to everyone. And I just appreciate your your energy and your vibe. I think that the space is a pretty fun, amazing, connected place to be. So I appreciate you being there. I am happy to be there because all of those things that you said, I feel like I'm getting those back in return. So it's just it's just a great time. Yeah, it's fun. Good. Yeah, I'm glad. Thanks for having this little chat with me. I appreciate you coming on my pleasure anytime. What did you guys think? Debbie is such a sweet heart, isn't she? It's just so fun to work with Debbie. So before I go, I want to share one final thought with you. In this conversation with Debbie, we focused a lot on her closet and what she's wearing now versus what she was wearing before and how she shops now and how she's filling pull together and how she pulls together outfits that make her feel incredible and cute. But what we didn't talk about was what's often happening behind the scenes in the work that I do with my clients. It's the mindset. Because yes, we're styling outfits and that's super fun. But more importantly, we're rewiring the way that you see yourself. So when Debbie and I started working together, like so many of my clients, she wasn't just unsure about what to wear. She was unsure about standing out, about taking up space, about seeing herself as someone that's worth investing in. That's what we work on together in my programs. Not just what looks good on the outside, but the beliefs, the patterns, the old stories that you've been carrying around that are keeping you playing small. Because style without mindset is just surface. But when you shift how you think about yourself, your wardrobe becomes a reflection of your identity, your leadership, your values, and just your amazing you. It starts to come out. So if you've been stuck in patterns that sound like I don't want to stand out, I don't know if I'm more spending money on. I'll feel confident after I lose weight. How many of us have said that one? That's the real work that we do together. Style is the vehicle. Confidence is the destination and the transformation. It's so much deeper than clothes. So if this spoke to you and you're ready to not just change your wardrobe, but change your life, reach out. I'd love to support you. Schedule a style consultation right now and we will get started. The link to schedule that style consultation is in the show notes and I can't wait to see you there. Bye. Thank you for tuning in to creating and shakeable self-confidence. In today's episode inspired you, let's keep the momentum going. Join the stylish professional, our exclusive Facebook community where ambitious women just like you are leveling up their confidence, style, and success. Inside you'll get pro styling tips, mindset shifts, and a powerhouse network of women cheering you on and stepping into their power. Just search the stylish professional on Facebook or click the link in the show notes. I can't wait to see you there and remember your wardrobe is a business tool. Make sure it aligns with the level of success you're aiming for. [Music]
Podcast Summary
Key Points:
Confidence starts in the closet
Shopping with clarity saves time, money, and mental energy by focusing on items that match your style and existing wardrobe.
Style transformation is "not hard, it's just new"
Client Debbie Oltson moved from safe, predictable clothing to adding color, patterns, and accessories, gaining compliments and confidence.
Tools like outfit challenges and style boards helped Debbie discover new combinations and identify wardrobe gaps.
Buying items that can be styled three ways reduces waste and prevents unused purchases.
Increased confidence positively impacted Debbie's business, making her feel more prepared to lead.
Taking the first step, despite feeling unworthy, leads to long-term savings and self-assurance.
Summary:
In this bonus episode, host Sherry Brasier interviews her client Debbie Oltson about her style journey. Debbie initially wore "safe" and predictable clothing—mostly neutrals like black and white—because she didn't know how to stand out or what colors suited her. She felt stuck and lacked confidence in her wardrobe choices, often buying similar items without purpose.
Through working with Sherry, Debbie learned to shop with clarity, focusing on pieces that align with her personal style and can be mixed into multiple outfits. Key tools included outfit challenges and style boards, which helped her experiment with new combinations, discover items already in her closet, and push her limits—like wearing a blouse she'd never tried, which earned compliments. Debbie now feels more familiar with her wardrobe, avoids aimless purchases, and saves both money and mental energy.
This newfound confidence extends beyond clothing, positively impacting her business by making her feel more prepared to lead and represent her brand. Sherry emphasizes that style transformation isn't difficult—it's just new—and that learning core principles turns the closet from a stressful place into a creative one. Debbie's advice to others is to take the first step, as investing in yourself leads to greater self-worth, long-term savings, and overall improvement in life and work.
The episode highlights three main takeaways: confidence starts in the closet, shopping with clarity saves resources, and style is learnable and fun.
FAQs
Sherry Brasier is an advanced certified style coach, personal wardrobe stylist, and seasoned hair stylist who helps women build self-confidence and dress stylishly.
The three takeaways are: confidence starts in your closet, shopping with clarity saves time and money, and it's not hard, it's just new.
Debbie felt her style was basic, safe, and predictable, wearing the same colors and types of clothes, and she didn't know how to stand out.
The outfit challenge and style boards helped Debbie see what colors and patterns to buy, and she learned to shop for items that work with what she already has.
The outfit challenge involves receiving an email each night with an outfit to recreate the next day using items from your own closet, helping you discover new combinations and identify gaps.
Debbie feels more confident and put together, which shows up in her business, making her feel more prepared to lead and helping her business grow.
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