My Top 3 Style Mistakes (and the Self-Image Story Behind Each One)

Style Reflects Self-Image

Most women think style is about clothes and I’m here to tell you it is about so much more. The way I like to define it is style is your inner thoughts about yourself made visible and it’s one of the most accurate self-portraits a woman paints of herself. It’s a daily public answer to the question, who do you think you are? It can showcase your values, your dreams, as well as your limitations and doubts, which means every style mistake a woman makes is not a fashion mistake, it’s a self-image mistake wearing fabric. And until you see that, you will continue to try to buy your way out of a problem that you cannot shop your way through. I know this because I made the three biggest style mistakes a woman can make and I did it for years and I want to walk you through what each one was actually doing to me underneath. So let’s dive in.

Welcome to the School of Self Image, where our motto is simple, elevate your self-image, elevate your life. I’m Tonya Leigh, your hostess, and I’ll guide you to become the woman who doesn’t just dream bigger. She lives bigger. Let’s dive in.

Today we are talking about my top three style mistakes and more importantly, what each one costs me on the inside. If you have ever blamed your closet for something your closet was not actually responsible for, this episode is for you. Here’s what I want you to listen for as I walk you through these three mistakes.

Mistake #1: Believing Style Requires Money

Style is not a layer you add on top of your life, it is a reflection of how you see yourself. The clothes you reach for in the morning, the things that you maybe save for one day, the things that you refuse to buy because they feel too good for you, all of that is a voting every day for or against the woman that you’re becoming. So when I tell you about my three mistakes, I’m not really telling you about clothes, I’m telling you about the three lies that I believed about myself and how those lies showed up in my closet first before sometimes they showed up anywhere else.

Your closet is honest, even when you’re not. So let’s talk about my first mistake. And that was believing that I needed to be rich to have great style. Now, this one is sneaky because it can sound so humble. It sounds like a reasonable thing to think when you grew up somewhere like I grew up. Style was for other women, the women in the glossy magazines or in Hollywood. It was for the doctor’s wives, the women with money. And that was something I didn’t have. It was for the women who lived in cities that I’d never been to. So I waited. I told myself the real wardrobe was coming after the next raise. And in the meantime, I didn’t try to understand my style because, well, I didn’t have the money, right?

So the things I did occasionally buy were just to keep me in clothes until one day I had the money. But here is what that was actually doing to me on the inside. Every morning that I got dressed, I was teaching myself a lesson and the lesson was beauty belongs to women with more money than you. You are not yet a woman who deserves beautiful things. You are not yet enough and you don’t have enough yet. And it turns out a life built on not-enoughness will never be enough, no matter how much money you have.

But for me, style had become this sort of class signifier in my head, which makes sense when I think about the little girl who grew up in a trailer and who was not really exposed to stylish women except on the screens or in magazines. So I had outsourced my sense of beauty, my sense of style, to my bank account. And as long as that was true, no amount of money was going to fix it because the woman who believes she has to earn her beauty will keep finding reasons she hasn’t earned it yet.

But then something interesting happened. I could see the pattern and I decided to stop waiting until one day and I started to make a few purchases of pieces that felt good. And I felt different wearing them and that energy started to expand, and the next thing you know, I had made the money and the very first thing I thought was, “Well, now I can finally be stylish.”

And what does a stylish woman do? She buys a designer handbag, right? Because that’s what stylish women carry. That’s how you signal that you’ve actually arrived. So I bought the bag and I will say that buying that first designer bag was symbolic because for years I could not muster up the courage to go into a designer store. I felt intimidated. I mean, come on, you have to be rich to go into those places, or at least that’s what I was telling myself. I thought they’re going to catch you and they’re going to kick you out. They’re going to see that you don’t belong. So yeah, that first bag was a sign to myself, you belong wherever you choose to enter.

But then there was another handbag and then another and I never really stopped to question my original belief that style equals being rich. But then what happened is I spent a ridiculous amount of money on a Jimmy Choo bag and a few months later I realized I don’t even like this bag. What was I thinking? And that’s when I had my wake-up call. Maybe I was wrong. Maybe money and style were two totally completely different things.

Now I’m not here to tell you that designer is bad. I still own some beautiful pieces that I treasure to this day. What I am here to do is to encourage you to question why you like them and if you really do keep on buying, but if you find that a big part of the reason is that you’ve been conditioned to think that a designer bag equals style or even self-worth, you’ve gotten it wrong. That is an inside job.

Just recently I noticed something really interesting. I’ve been reaching for my cute white shoulder Tory Burch bag that I bought for $200 at the outlet and I’m choosing that over the more expensive ones. And the reason being is that that one is my favorite. I love how it goes with everything. I love how cute it is. It’s a perfect size. It is the quintessential summer handbag. I love it, plain and simple.

Think of it this way, if you were to put a lineup of bags in front of you, you had no idea who the designer was, how much they cost, where they were made, and you simply were choosing based off of what you love, which one would you choose? And for me, it’s the Tory Burch bag. Well, along with my Dior bag, I do love that one as well, but it’s not because of the label. And this is what I want every woman listening to hear, when you factor the cost of things out of the equation as a signal of style or status, you finally begin to notice what you actually love and what you don’t.

And for me, what I discovered was that I do love certain designer things, but not nearly as much as I thought I did. Some of them I’d only ever loved through the lens of what they were supposed to mean. Once that lens came off, the love was gone and what was left was just a very expensive bag that didn’t actually agree with me. The price tag had been kind of a noise. As long as I was listening for what was expensive, I couldn’t hear what I truly loved. And taste, real taste, only starts to sharpen once you stop using cost as a stand-in for your worth.

Style has never been about money. Some of the most stylish women I have ever known didn’t have a lot of money. What they did have was a strong sense of self and a point of view. A woman with a thousand dollars and a clear sense of self and what she loves will out style a woman with $20,000 and no idea who she is, every single time. So that was my first style mistake.

Mistake #2: Outsourcing Personal Taste

Now let’s talk about my second one that I didn’t recognize for a long time because for years I thought it was a virtue, and that is I outsourced my taste. I let other women decide what was beautiful, what was flattering, what was me. The magazines, the influencers, the media, the well-meaning friends who knew what was in and what wasn’t, anyone but me. And now we have a new one, AI. Women are uploading photos of themselves and asking a chatbot what they should wear, what colors flatter them, what their personal style is. They’re asking a piece of software to tell them who they are. And listen, I’m the last person to be anti-AI. I use it every single day. It’s one of the most extraordinary tools that we’ve ever had, but there’s a difference between using AI as a creative partner and using it as a parent.

And that’s what I see happening. Women are looking for someone, anyone to tell them who they are and what they love instead of doing the harder, slower, more intimate work of getting clear on that picture themselves. It’s kind of regression. A grown woman who’s accomplished in every other area of her life asking a screen, “Please tell me what I like. Please tell me what I should want. Please tell me who to be.”

And here’s what I think is actually going on underneath. So many women feel disconnected from their own lives right now. They’re restless in ways they can’t even name and they assume something is wrong with them. It isn’t. The disconnection is merely a symptom. What’s happened is you haven’t connected with what you love. You’ve connected with other people’s loves, what the algorithm rewards, what the influencer wore that week, or what the chatbot suggested when you uploaded a picture of yourself looking for an answer and then you wonder why your life feels like something’s missing.

Of course it does. You’re not living your taste, you’re living a borrowed one. So every time I went shopping back then, I would have a phone in my hand and someone else’s eye in my head. And then I’d get home with a pile of things that made no sense, something that didn’t feel right for me and I’d stand in front of my own mirror feeling like a stranger. Here’s what outsourcing my taste was doing to me underneath, it was rehearsing this belief that I could not trust myself, that my own perception could not be trusted, that the answer was always somewhere else, in someone else’s eye.

And the more I rehearsed that belief in my closet, the more it leaked into the rest of my life. I stopped trusting my taste in food, in my home, the muscle of knowing what I loved had atrophied because I wasn’t doing the reps and that’s the thing about taste. Taste isn’t a gift. It’s not something you’re born with. It’s a muscle that you train and every time you outsource the decision, you skip the rep. Every time you reach for your phone instead of your own eye, you teach yourself that you are a follower, not a taste maker and the closet keeps the receipts.

Now listen, inspiration is a beautiful thing. You need to go and get it. You don’t know what you don’t know. You have to expose yourself to the world and to life and to style to understand what’s even available. But at the end of the day, it is up to you to decide if it’s for you or not, and if it is, what is your version of it? To be a stylish woman, you must decide for yourself what you love, what you value, what your needs are, what your future looks like, and more importantly, who is that version? Living it. Then you have to be courageous enough to choose for yourself.

Mistake #3: Waiting for the “Right” Body

Now let’s talk about my third style mistake and it’s one of the hardest to admit because almost every woman I know has been here and almost no one talks about it. I thought style was a body size or a certain body shape. I thought style was something I’d get to have once my body had cooperated, once I had lost the weight, once I got back to a size that I’d been in my early 20s, once I looked like the ’80s supermodels, then I could finally be stylish. Until then, I lived in what I call “waiting clothes.”

I want you to sit on that phrase for a second, “waiting clothes,” the clothes you wear while you’re waiting to become someone else. They’re not ugly exactly, or at least mine weren’t, they’re just neutral enough not to draw attention to a body that you have decided as a problem. They’re the wardrobe equivalent of holding your breath. And here’s what living in waiting clothes was actually doing to me. It was teaching me every single day that I was not enough right now, that the real me was somewhere on the other side of a smaller dress size.

And that belief did not stay in my closet, it walked out into the rest of my life. I stopped getting into photographs. I stopped saying yes to dinners. I started shrinking, not in size but in my own presence. And guess what a woman living like this often does? She overeats. She becomes really good at proving herself that she’s not enough because that is how self-image works. You will always subconsciously work to prove yourself true. But here’s what I want you to hear because this is the part that most women miss, a different body cannot change your mind. You must change your mind first. If you don’t, you may end up losing the weight and still be miserable. That was me.

I actually literally starved myself from a size twenty to a size two. And guess what? I still didn’t feel enough and certainly I didn’t feel stylish because I never asked myself, “What do you love?” Now I was just smaller and afraid of putting the weight back on and eventually I did, until I learned the power of self-image and that’s when I saw the cycle and I couldn’t unsee it. How many times have you hit a goal only to find a new thing that you need to fix? You see, the mirror will keep finding evidence because the mirror was never the problem. The mind was.

Style is not what you get to wear when your body finally cooperates, style is the practice of getting to know the body you have today, your body type, what looks best on you, and then treating that body like she’s worth dressing well. And it just so happens that when I started to think and live in this way, I finally lost the weight and I’ve kept it off for years all because I stopped waiting on the weight. 

The Real Problem Beneath All Three Mistakes

So let’s look at all three of these mistakes together and what they have in common. Believing style required money that I didn’t have, believing that style required taste that I didn’t have, believing that style required a body I didn’t have. They are all three different sentences, but they all share the same lie. And the lie is this, that style belonged to someone other than me, someone richer, someone thinner, someone who was more sure of herself. Every one of those mistakes was a way of telling myself I wasn’t that woman yet, and as long as I wasn’t that woman yet, I didn’t have to take the risk of becoming her. That’s what was really going on inside of my closet. It was never, ever about the clothes.

Now, here’s something that I want you to do. I want you to imagine getting dressed tomorrow morning. You walk into your closet without bracing yourself. You don’t bargain with the mirror. You don’t perform the small ceremony of self-criticism that most women perform before getting dressed. You reach for the piece that makes you feel the most like your most expansive self, not the safest one, not the most forgiving one, the one that agrees with the woman you’re actually becoming, and you put it on and you walk out the door dressed like a woman who has decided that her life is happening right now.

Style Begins With Self-Trust

That’s the woman that this work points toward. She isn’t a size, she’s not a budget or somebody else’s idea of beautiful, she is a decision. Here’s what I want you to try this week and it’s not probably what you expect. I’m not going to ask you to clean out your closet or make a Pinterest board. I don’t want you to buy a single thing. I want you to spend some time this week just noticing. Every time you get dressed, pause for 10 seconds before you walk out the door. Look in the mirror and ask yourself, “Do I actually love this?” That’s it. No grand decision, no closet purge, just a week of you noticing what you actually love. Because that’s the part that most women don’t realize, you can’t shop your way back to yourself. You have to listen your way back and the listening starts with a small daily noticing of what you love and what you don’t and that knowing is actually where style begins.

So remember, style is never just about your style, it is one of the clearest mirrors that you have about your self-image. So if your closet has been telling you a story that you don’t love, don’t blame the closet. You need to address the woman who is buying for it. And if you want help with that editing, I want to invite you to something. Every week I write a letter called The Edit. It’s a place where I share the small specific suggestions and ideas on how to elevate your self-image week by week, one shift at a time.

Some weeks it’s about your closet, other weeks it’s about your home, some weeks it’s just about managing your mindset or looking at the standards that maybe you’ve stopped holding. You can go to schoolofselfimage.com/edit. I’ll also post the link in the show notes. All right, my friends. Have a beautiful week and I’ll see you in the next one. Cheers.