My Top 5 Style Mistakes (and What They Taught Me)

Have you ever stood in front of a closet full of clothes and still felt like you had nothing to wear? I think we've all been there. And today we're going to unpack the reasons behind this all too common frustration because I am sharing my top five style mistakes. The fashion faux pas that kept me from truly expressing myself through my wardrobe and what I did about it. So let's dive in. 

Welcome to the School of Self-Image, where personal development meets style. Here's your hostess, master life coach Tonya Leigh. Hello, my beautiful friends. Welcome back to the podcast. It is eight o'clock in the morning and I've already been up for a couple of hours and so I'm feeling so motivated that I had to jump in here and record this for you. I'm feeling motivated because this morning I had a chance to sit down and journal and sometimes I just check in with myself and ask, what do you want to think about?

Where do you want to place your attention? And I wanted to think about my own style story because in case you missed it, I declared that this would be my summer of style. And so this morning I went on a little journey to Young Tonya, when she was first starting her style journey. And all of the lessons learned and all of the mistakes made. And it's all been beautiful, it's all led me to here. It's been quite the journey of self discovery because style may seem superficial on the surface, but in reality it's so deep, it's so deeply linked to our essence, our personality, our identity, our self image. And when you start digging deeper into your style choices, you may be surprised at what you've outgrown and who you no longer are when you're truly being honest with yourself. And I have personally felt that shift over the last year or two.

And so this deep dive into my own style journey is what inspired today's episode. I was taking notes, I'm like, I have to do a podcast on this. And these aren't just random fashion faux pas that I'm going to be sharing with you. These are hard earned lessons, moments of clarity, and yes, sometimes cringe-worthy moments that have shaped my style philosophy. It's also what led me to create the style experience. And looking at all of the style programs out there, I felt like something was missing. I felt like they weren't going deep enough to really use style in a way that I think it was meant to be used, as a form of self-expression, but also as a tool for self-discovery. And that's what makes the style experience so unique is that yes, we cover timeless style principles, but more than anything, I want style to be a gateway into you being your most confident, most fully expressed self.

And the only way to do that is to really go deep into what you love, what you truly value, your personality, what feels good for you, what lights you up. And in watching women go through this experience last year, I've seen how it spills into every area of their life. Not only does it do things like help you save money and time, but the confidence that's gained, the just peace in one's life because you're no longer wrestling with your closet and ultimately your self, it is invaluable. And so the style experience is opening its doors for enrollment really, really soon. And I am so excited to work with this group of women over the course of six months. Because listen, Rome wasn't built in a day and neither is a great wardrobe. We are going to have so much fun. And I can't wait for you to really dig deep into your style story.

And more importantly, I can't wait for you to write a new one because that's what we're going to be doing in The Style Experience. So if you were interested, stay tuned. It's coming really, really soon. Now, for today, I want to share my top five style mistakes because I believe we can turn these mistakes into success stories. I often tell members of the School of Self-Image. I'm like, listen, you got to make mistakes to succeed. Success is built on a mountain of failures. That is not my quote. I've heard it many times from different sources, but it's true. And so let's start with mistake number one. And I know that so many of you have done this and maybe you're doing this right now, and you got to stop. And I call this the waiting game. I did this for years. What this looks like is waiting for your body to change, to invest in your style.

You keep telling yourself, as you're standing in front of the mirror, "You know what? When I lose those 10 pounds or 20 pounds, then I will buy something that looks good on me." Or once I get through menopause, then I'll focus on my style. I've been there, I've done that. And I can tell you on the other side, it is a recipe for misery. And let me share with you why. Everything you choose is confirming a story about yourself. So everything around you, your home, your friends, your job and the clothes you wear are creating the story that you have about yourself. And so when you are choosing, let's say, big, baggy clothes to hide your body like I used to do, what is that confirming? That you probably have a weight problem when you choose clothes that don't look good on you. Because in the back of your mind, you're telling yourself, I'll do it later when I've lost the weight.

I don't want to waste that money. But go deeper and think about what does that confirm about you? You start creating this narrative that just feeds on itself and it's so hard to get out of until you start making new choices. I often say I started changing my life with one dress. I was very much in this place of waiting. I had Sarah, she was probably about two or three years old, and I was still carrying a lot of the weight. And if I wasn't in my nursing scrubs, I was just wearing big baggy khaki pants and an oversized white T-shirt. And I had this story, when I lose the weight, then I'll invest in something that looks pretty. But every time I would look in the mirror, I just feel terrible about myself. And when I felt terrible about myself, I felt hopeless. And then I would overeat.

I would give up. I wouldn't take care of myself. And so you can see I was just this self-perpetuating story that I kept living out. And one day I realized what I was doing to myself. And this was before I had the tools that I have now, but I could see it. I didn't have the theory behind it, but I knew deep down, "You got to do something different, Tonya, because this isn't working." And I found a very lovely simple little black dress. A little black dress saved my life. And I put it on and I remember wearing it. And I remember even Sarah looking at me and saying, "Mama, you look so pretty." I wasn't used to her saying that because that's not who she was seeing. But I felt a little shift that day and that's all we need, ladies, just a little shift, little shifts add up to create big shifts.

And I started paying attention to not only my clothing choices, but a lot of the choices in my life because I knew I needed to create a new story about myself. And so I want to challenge you all that are waiting, waiting to invest in your style, waiting to buy that dress. Please stop. It's not serving you at all. And here's what I've learned as a woman. Our bodies are constantly changing. We've got pregnancy, we've got perimenopause, menopause, lifestyle changers. Our bodies are always in flux. So waiting for the perfect body is like waiting for a train that never arrives. I believe style is for now. Your style is an expression of who you are today, not who you might be in six months or a year. Also fit is everything. Clothes should fit you, not the other way around. Proper fit can make a $20 dress look like a million bucks while a poor fit can make even a designer dress look sloppy.

And finally, self-love is stylish. Embracing and dressing your current body is an act of self-love. And confidence, well, that's the most stylish accessory you can ever wear. I want you to remember this. Your body isn't the problem. Ill-fitting clothes and unrealistic expectations and waiting, that's the problem. And so start dressing for the wonderful woman that you are right now. In fact, if you are one of those women who you've been waiting, I'm going to challenge you, actually. I want you to find one outfit that fits the body you have right now and looks amazing on you as you are right now. It might be something that you already own and maybe you need to take it to the tailor or it might be something you need to go out and find. But don't hold yourself prisoner to this ideal. Because at the end of the day, women want to feel beautiful.

And that is available to all of us right now today. We don't have to wait until one day when. We have to change our mindset. We may have to redefine what beauty is for us. But when you do, you take all of your power back. Waiting takes your power, but the moment you stand up and you say, "I'm no longer waiting to feel beautiful, to live the life that I want to live." That's when you get all of your power back. And when you have your power back, that's when your life begins to change. Now let's talk about mistake number two. And I'm calling this the numbers game, and this is that misguided belief that having more clothes equals having more style. And I fell for this one big time years ago. I remember during a move, looking at my closet, it was bursting at the seams.

I still had tops with tags, dresses I'd never worn, jeans in every wash imaginable, so many shirts and sweaters. And yet the crazy thing was every morning I'd stand in front of my closet, utterly paralyzed. Isn't that crazy? So much abundance and feeling so much scarcity. And I would tell myself, I have nothing to wear. And my friends and family, they were confused. They're like, "What are you talking about? You have so much to wear." But when I was packing up box after box of clothes, I realized I couldn't remember wearing half of them. The sheer volume was so overwhelming, and yet I had nothing to wear. And that's when it hit me. I had plenty of clothes, but I had no real style. There's a big difference. I thought the answer was to buy more. If I buy more clothes, I can figure out my style. But I had it wrong.

Because more isn't always more. A closet full of mediocre pieces or pieces that don't really fit you, either your body or your essence, they won't serve you well. Also, quantity mask indecision. Often we buy in bulk because we're not sure of what truly suits us. When we're confused, we may buy more than we need or more of the wrong things, hoping that that quantity is going to fix the problem, but it never does. And then decision fatigue is real. Too many options can actually make getting dressed harder, not easier. And then quality over quantity, always. One well-made versatile piece that fits your style can be worth 10 cheap trend driven items that don't fit you, that you just bought because they were on sale or you saw a friend wearing it looked cute on her. And the lesson that I've learned in this is your style isn't defined by the quantity of your clothes, but how well they reflect and serve you.

It's about having less but loving and wearing it more. Mistake number three, I call the label trap. This really hit the wallet, ladies. And it's this belief that designer labels automatically equate to great style. And spoiler alert, they don't. Now, this may seem paradoxical to what I was just saying about quality. I do believe in quality, but quality can be obtained without spending thousands of dollars. And it doesn't mean designer labels. I think back to this dress that I bought. It was my first designer dress. And it was beautiful. And I spent a lot of money on it. But the problem was it didn't quite fit my body. I was trying to make it work. It didn't fit my lifestyle at the time, and it definitely didn't fit the other things in my closet. And so it was just hanging in my closet, becoming more a source of anxiety than a source of joy.

And I believe everything comes down to intention. What's the intention behind what you do? And when I got really honest with myself, my intention was I was trying so hard to be stylish because I didn't really know what I was doing at the time. And so I thought, "Well, it's designer. It costs a lot of money. Obviously it must be stylish." Well, it wasn't obvious to me that it wasn't. And so I share that with you because I do think that when women go on a style journey, they automatically start running stories that it's going to be expensive and they're going to have to have a lot of designer things. If you love designer truly, and you have a particular designer that you love their clothes, you love their bags, you really feel like they represent who you are, fantastic. I will always, always encourage you to do what feels like love, joy, and abundance.

But I've just seen too many women choose designer clothing because of the illusion that they think they're going to create to other people in being more stylish. And it ends up having the opposite effect because when you're decked out head to toe in labels, it almost signifies that you don't yet know your style that well. That you are depending on and leaning on these labels to do the work for you. And that may sound a little harsh, but it's what I know to be true for me. Maybe not for you. Maybe you love being decked out head to toe labels. But I have found that the most stylish of my friends are those that have a mix of high street brands and thrift store finds. They choose things that fit their body, their coloring, their personality, the labels don't matter. They're fit and their confidence does.

And so in all of this, I've learned that style isn't something you can buy as something that you cultivate and express. And expensive doesn't always mean better, especially if it doesn't suit your lifestyle or your body. I've also learned to mix high and low. Some of my most stylish outfits combine budget finds with a few well-chosen luxury pieces that I've collected over the years. And finally invest in quality, not labels. A well-made piece from an unknown brand could outlast a poorly made designer item. So learn how to spot quality, quality fabrics, quality stitching, because that doesn't necessarily mean a lot of money. So the takeaway here is true style isn't about the label, it's about how you wear it. It's about choosing pieces that resonate with you regardless of the price tag. And remember, confidence is the best designer label you can wear and it goes with everything.

Mistake number four is keeping myself trapped by a self-image. All of work I do is around self-image, and you can have a healthy self-image and an unhealthy self-image. You can also get trapped by a self-image. And I saw that in myself because this goes deeper than just the clothes, ladies, this is about identity. It's about clinging to a version of yourself that you've outgrown or worse, a version that never was you to begin with. And so for years as I was figuring out my style and I was on my own style journey, especially in the very beginning, I would dress for what I thought others expected me to be. So when I would go to networking events, I would put on something that seemed very professional, even though it did not look like me at all. It didn't feel right.

If you ever put on an outfit and you're like, "Okay, this looks good, but it doesn't feel good. It doesn't feel like me." And then talking about the last mistake, I found myself caught in this trap of designer clothing labels. Because I had somehow created this brand of luxury. And now I had the pressure of thinking, "Oh my God, now we've got to buy luxury all of the time." When in fact I do love some luxury. There are some pieces that I have right now that I am so grateful for and I'm so glad that I purchased them. I have worn them for some of them for over a decade. They have served me well, but I don't want to be trapped by anything. I don't want to be trapped by this image that doesn't allow space for me to grow and to evolve. Even if I think about doing the style experience, I love style.

I think it's so much fun. But I could easily become trapped in this notion of, oh my God, I always have to look stylish and that means this, this and this. And before you know it, I'm living a life of performance versus a life of authenticity. And I just refuse to do that. That's why I will warn some of you all, if you see me in Whole Foods in Charlotte, you may find me in my yoga pants. Now, hopefully they're very cute and well thought out, because that just makes me happy to put together outfits that really feel good, whatever that means for that day. But again, notice how you may have trapped yourself thinking that you have to be a certain version of yourself because that's what others expect you to be. And for me, I have decided that true style is about being comfortable in your own skin and your life, not in someone else's expectations.

Here's what I've learned from that mistake. Your style should evolve as you do. What worked for you five years ago might not reflect who you are today, and that's okay. In fact, I would challenge you to consider that it's a beautiful thing. It means that you are growing as a human. Also, we've already talked about this, but quality doesn't always mean expensive. I discovered that designer labels don't mean nearly as much to me as they used to. I still love quality, but that doesn't mean it should cost thousands. And then authenticity is magnetic. When you dress in a way that truly reflects you, people respond to that energy. And then finally, expectations are often self-imposed. Most of the time the person putting the most pressure on you is yourself, and most people are not even paying attention to you actually. And so free yourself. Free yourself to explore and grow with your style because your style should be reflection of who you are now, not who you used to be.

It's okay to let go of the old to make room for the new. And remember, the most stylish thing you can wear is your authentic self. And this leads me to mistake number five, and I'm calling this one the knowledge gap. And this is the misconception that style is something that you're born with, not something that you learn. And that's what I thought. I thought for years that some women have it and some don't. And boy was I wrong about this one. In fact, when I started to talk to my stylish friends, what I discovered is that most of them grew up in stylish environments. So their mother had a sense of style or their aunt or their sister, they were exposed to it. So it was something in their environment that they learned. And that's what I want you to know. Style is something that you can learn. Because I remember being just feeling I was drowning in fashion magazines, trying to replicate outfits exactly as I saw them.

And the result was I looked like I was wearing someone else's clothes. I felt like a fashion imposter, convinced that I just didn't have the eye for style. And yet, if you all think about it, style is something that we engage with every single day. Every single day we wake up and we get dressed. And so we want to feel like we're good at it. And so we do all of these crazy things like spend a lot of money on things. We collect a lot of clothes. And for me, I even hired a stylist. I thought, for sure this is the answer. And the problem with that was that she didn't really know my style. She could look at me, and I answered some questions for her and she pulled some things for me, but then I ended up putting them on and a couple of things I really liked, but the majority of it just felt off.

And listen, I believe in hiring a stylist once you've figured out what your style is. When you want to save time, you want someone to go out and pull pieces for you. I think that's when a stylist is such an incredible asset. But if you depend on a stylist, that means that you're always going to be turning to her to tell you what looks good on you. And this is what we do in life. Think about it. We turn to other people, tell me what to do. Tell me where I should go. Tell me if I should date this guy. Tell me if this is a good idea. And every time we do that, we lose trust with ourselves. And that's what I was doing with style. I was outsourcing my style in hopes that someone could save me. When in reality, style is such a learnable skill.

And I will never forget reading this book. It was many, many years ago. So if you ask me what the book is, I can't even begin to figure out how to tell you because it was so long ago. But I remember going through this book and thinking, huh, this is a skill set. So if I take some time to learn this skill, then everything else as it relates to my style and my closet will become so much easier. And it turns out my theory was right. Style is a skill. Like any skill, it can be learned, practiced, and improved upon. And knowledge is power. Understanding the principles of style empowers you to make better choices. Also, rules are made to be broken. But you need to know them first to break them effectively. Personal style is a journey. It evolves as you learn and you grow.

Style education isn't about conforming to rules and trends. It's about gaining the tools to express your unique self fully and confidently. And again, this was the piece that was missing. I think if I could do one thing differently, it would've been to learn this early on. I think about all of the money I would've saved, the better outfits that I would've put together, that would've felt more true to me. That would've happened much sooner had I put style education at the forefront of my journey. But again, no one told me this. No one told me, "Hey, listen, Ton, you can learn this." I did it through a lot of trial and error, seeing what works, what doesn't. I then went on to study this professionally, but I wish I would've done it sooner. Because again, I think about all of the days and nights in my closet thinking I have nothing to wear.

I can think about the drama of packing for trips and how much anxiety I had. I can think about all of the money wasted, and I don't like to think of wasting money because I think money is a renewable resource, but when you have clothes in your closet that are just hanging there with tags still on them, there is a misuse of your resources. And I personally was guilty of that, and that was part of my learning journey, so I don't beat myself up over it. However, style education, if you're someone who is struggling in this area of your life and you really want to feel empowered, you want to feel amazing in your clothes, you want to understand how to shop better, you want to save money, actually. Style education is so important. And so there you have it, my friends, my top five style mistakes.

If any of these resonated with you, remember, awareness is the first step to change. We've all been there. And the journey to personal style is just that. It's just a journey. When I look at each of these mistakes, what I know is that they have taught me valuable lessons about not only style, but self-expression and self-love. They were actually the catalyst to me creating the style experience where we go much deeper into the journey of style. And it also inspired me to create something else for you all. I'm so excited to share this. In case you did not hear, we are about to host a free five-day style challenge. It actually starts tomorrow, and this is where you're going to learn small timeless style principles each day that you can apply immediately to elevate your personal style. I created this challenge because I've done style challenges in the past that I couldn't relate to.

Actually, some were telling me to pair florals with stripes and to do things that didn't resonate with my particular style. And so I wanted to create a challenge that no matter what your style is, no matter what your budget is, no matter where you live and what your lifestyle is, you can learn something from this. Again, small timeless style principles that we are going to be practicing each of these five days. So if you want to join us, all you have to do is go to schoolofselfimage.com/stylechallenge. All together, schoolofselfimage.com/stylechallenge, and come join us.

We're going to have so much fun. And I hope I get to see you in the challenge. And remember this, style isn't about perfection. It is about authenticity. It's about joy. It's about waking up each day, opening your closet, and seeing a reflection of the amazing woman that you are. And don't be afraid to make style mistakes. They are a part of the journey. But if I can support you at all in limiting those mistakes, I would love to. And that's why I think that you're going to love the style challenge. So again, go to schoolofselfimage.com/stylechallenge. I will see you there. We start tomorrow. And hopefully I will see you on next week's episode. Cheers.