Jennifer Mackey Mary: Celebrity stylist Rachel Zoe famously once said, style is a way to say who you are without having to speak. I totally agree. But what happens when your style isn’t saying the right thing? Sometimes your style is telling people who you used to be rather than who you are right now. And other times it’s not telling people anything about you at all.

So today we’re talking about what personal style really means, how to recognize when yours needs some attention and maybe even a change, and how to create a wardrobe that feels more like you. Let’s get started. 

Welcome to the Everyday Style School, the show that teaches you everything your mom never did about getting dressed. I’m your host, Jennifer Mackey-Mary. After 25 years of dressing women with real bodies, real budgets, and real lives, I know great style isn’t about following one-size-fits-all advice. It’s about learning what works for you. 

Hello, gorgeous. 

Well, we have got our first change-up of the season happening today. You might know that I love making a plan. I am a planner. But did you also know that I love changing that plan whenever the mood strikes? What can I say? It’s part of my charm. My team loves it. They truly do. 

Originally, I was supposed to talk about navigating weight changes stylishly, which is a very important topic that a lot of women struggle with, I know. But honestly, after sharing my lessons of overhauling my wardrobe because of weight in the last episode, I just couldn’t handle talking about myself or my body or my wardrobe again. I have had enough of me for a while, and I know that episode is going to hit a lot closer to home.

So today I’m just switching it up and talking about a topic that I could talk about all day every day and that is personal style. In fact, I have talked about it quite a bit on this show and in the show notes I’m going to link to a couple of my favorite personal style episodes so you can check those out if the mood strikes you. 

For me, talking about personal style is fun because style is supposed to be fun. Style isn’t supposed to be something that feels like a long, hard, day in, day out slog, but often that’s what it turns into, full of shoulds and rules and am I doing this right and can I wear this? And frankly, I just find all of that so exhausting. Because style at its core should be enjoyable because it’s about embracing what you like and who you are.

And that’s what I love about it so much. Personal style isn’t right or wrong because it’s yours. And no one can tell you that what you like or what you don’t like is wrong. 

But I want to talk about this idea for a minute, because if I don’t, I worry that what’s going to happen after this episode comes out is that every single question our members ask in the Style Circle community will be answered with, well, if it’s your style, wear it, or if you like it, wear it, or just wear what you love. You get where I’m going with that, right? And there are times when that is the right answer. There are times when that is the only answer. 

For example, do you like this dress? That’s the kind of question that people ask me or have asked me for literally decades and the only correct answer is It doesn’t matter if I like it or not. If you like it, wear it. Or is this top cute? If it is your style, you should wear it. When it comes to opinions on style, the only one that matters is yours. 

So I want to be very, very, very clear that I think you should 100% hands down in every single situation wear what you like and wear what makes you feel good. I want there to be absolutely no confusion on where I stand on this. I’m on the record saying that, right? You all heard it? Good. Okay. 

With that said, though, the answer to every style-related question can’t be just wear what you like. Let me give you a few examples that I have seen asked over the years. Do these pants fit well? Just wear what you like. Does this dress highlight my tummy? Well, if you like it, wear it. Are these shoes current? You should wear what makes you happy.

This drives me crazy for a few reasons, but the biggest one is that that wasn’t the question that was asked. People know they can wear dated shoes or ill-fitting pants or a dress that shows off their belly if they want to, but there is an objective standard for the way pants should fit. There’s an objective standard of which parts of your body address emphasizes. There is an objective standard of what’s current and what’s not. It doesn’t mean you have to follow it, that is totally your choice, but it doesn’t mean the standard doesn’t exist. 

I especially see this around, is this current or is this dated? Look at any post, any YouTube video, anyone asking the question in our Style Circle community on this topic, and there will be someone who says, well, if you like it, wear it, or I don’t follow trends, I just wear what I like. And honestly, I love that journey for you, I truly do, but it is okay to wanna look current. It is okay to not know if something is current, and it is okay to ask. 

The reason I bring this up is that the response, just wear what you like, as a go-to in every situation, tells me something very, very important, which is that we often have a hard time distinguishing between the subjective part of style and the objective part of style. And I’m going to explain what I mean, and I’m probably going to ruffle some feathers. So strap in friends. Here we go. 

There is a difference between personal style and good style. Yeah, I said it. There is a difference. between personal style and good style. They are not the same thing, but I see a lot of women who think that they are or don’t know there’s a difference or women who solely rely on one and completely ignore the other and then wonder what’s missing. What’s missing is almost always one side of the style equation. 

Personal style is completely subjective. It’s just what you like, and that can never be wrong. If you like bold patterns and bright colors, great. If you like neutrals and solids only, fantastic. Personal style is an outward expression of your personality, of who you are and what you want people to see. And that, my love, is never, ever, ever right or wrong. It’s just you. 

Good style, on the other hand, is largely objective. It relies on elements of design like balance, composition, color theory, lines, texture, and proportions to create a cohesive, aesthetically pleasing result. 

I want you to think about art for a minute. Art is highly subjective, right? My family has been going to a lot of museums lately and I have really discovered after 20 some years together how different my husband and I are when it comes to what kind of art we like. That man loves a still life, loves it. Give him a landscape or a 300 year old painting of a Flemish woman and some ducks and he is happy. I, on the other hand, love abstract and modern art. Colorful, bold, the bigger the better. Neither of us is wrong. It’s just what we like. It’s different, but it’s not wrong. Art is highly subjective. But if art was totally subjective, why do art schools exist? 

Since the days of painters from Flanders and even much, much earlier, people have learned to produce good art and get better at their craft. I don’t love all those landscapes and still lifes, but I can recognize the skill and the talent that went into creating them. I can appreciate that something is good art without personally liking it. If I tried to make you a piece of art, even the abstract paintings that I love so much, it would not be good art. I can guarantee that. 

Sidebar story, when I was in second grade, the art that I produced was so bad that my teacher used to like hang our artwork in the halls and she used to hide mine behind other kids’ artwork. That’s how bad of an artist I am. So I know what I’m talking about here. Okay, so my art that I would produce for you, not good art. I might love those abstract paintings, but I don’t know and I haven’t practiced the fundamentals of creating good art.

Those fundamentals that are necessary to producing an end result that is aesthetically pleasing. But on the other hand, you can learn all the fundamentals of creating good art and you can follow all the rules, but if you have no point of view, nothing that makes you stand out, what you’ve basically created is a paint by numbers. It’s nice, it’s fine, but is it saying anything about you? 

So what I’ve seen over the years is women picking a lane. We have the, just wear what you like crowd. And they have wardrobes that have tons of personality. They’re definitely them, but they’re lacking in technical know-how. And then we have the, did I do this right gang with clothes that fit well and are technically good, but they have no personality. It’s like anybody could be wearing them. Here’s what I want you to take away from this. Great style combines the two. 

Great style says, this is who I am, this is what I like, and this is how I want to look. And then uses the objective design elements to bring that look to life. Think about a woman you know whose style you admire, someone really, really stylish. She probably doesn’t wear exactly what you would wear or maybe not what you would wear at all, but she probably has a clear defined point of view that is executed well technically, right? That’s great style and that should be our goal.

So obviously, personal style is clearly a favorite topic of mine. But even so, this episode almost didn’t make the cut for the season. Do you want to know why? Originally, I planned on talking about how to change your personal style. This is a season of talking about changes, right? But I wasn’t sure if there are enough women listening who have a personal style to change. You have to have something before you realize it no longer works and you have to change it, right?

And to my style members who are listening right now and might be feeling a little bit personally attacked, like, you don’t know what you’re talking about, woman. I took the class. I picked my three words. You don’t know me. That is true. I don’t. But let me ask you this. What are you doing with your words? Are you using them to hone your style? Are you looking at your wardrobe and saying, what is missing? What part of my style is missing and what do I want to develop more? And are you looking at things that you are thinking about buying and asking yourself, Which part of my style does this speak to? Which will this help bring to life? Or did you just obsess over choosing the perfect three words, never ever to think about them again? I don’t know the answer to that, but if I just touched a nerve, I think you do. 

The truth is most women lack the personal style part and then try to make up for it with the good style part and think they can get to great style through endless rules and wondering if they’re doing it right. Do you remember when I said I see style being exhausting for a lot of women? This is what I’m talking about. This is a big reason why. When you take the personal part out of personal style, you take a lot of the fun out. 

And this is why inside the Style Circle, our framework teaches personal style before body shape, before the fundamentals of good outfits, before anything you can get right or wrong. Because we believe that style is personal and it should be fun. 

So I took this episode off of this season’s list but then I put it back on because it’s fun and I like to talk about it but also because there are a lot of similarities between having a personal style that just doesn’t resonate with who you are anymore and not having one in the first place. Both start with a closet full of clothes that just don’t light you up and a desire for something more. A desire to feel stylish, to feel like your clothes represent your authentic self and for your outsides to represent your insides.

So whether you are changing a well-defined sense of personal style or you are going from not having a clear point of view to having one, the lessons and the strategies remain the same. So I put it back on the list for this season of changes in our style over our lifetimes. Okay, so how do we do this? How do we define personal style? How do we get a personal style? How do we change all that good stuff?

The first step is to decide if personal style is really the issue that needs changing at all. And there are three simple ways you can tell. 

The first one is, if you are working too hard to achieve the style you want, you might be on the wrong path and it may not fit anymore. A lot of women have an idea of how they want to look, but making that happen in real life day to day on a random Tuesday is just too much effort. And when I was thinking of putting this episode into the lineup for the season, I went to our community and I asked women who had changed their personal style how they knew it was time for a change.

And by the way, members, that thread is a gold mine of insights. Go check it out. I have pinned it to the featured post so you can find it easily. but I want to share a few of the responses with you. Katie said she was chasing a style that just didn’t work easily with her body shape. Misa said her desired style would have required way more trial and error than she was willing to do and a much bigger wardrobe than she wanted. Amelia said her desired style was more aspirational than what worked for her life. Now, I believe you can have any style you want for any lifestyle. That is a huge confusion women have. We’ll talk about it later. But the bottom line is, if it feels like too much effort or too far away from who you are, it’s probably time for a realignment. 

The second sign is that the clothes you used to love don’t feel like you anymore. I am a person who updates her wardrobe frequently. Let’s just call it an occupational hazard. I would also describe my style as current, which means that my closet turns over more than most people’s. But this is different than just updating or getting rid of things that are no longer current.

What I’m talking about is that you no longer gravitate toward the kinds of things you used to love or the looks you used to love. And let me give you an example. Let’s say you are a woman who historically has lived in jeans. Jeans have always been your thing. They’re your go-tos. And you’ve gotten rid of your ripped jeans and your skinny jeans. You’ve replaced them with this season’s dark wash wide legs or barrel legs. But even so, you’re not automatically reaching for jeans anymore. You are grabbing trousers every day instead, even if you’re just running errands. 

One item here or there doesn’t mean that your entire style has changed, but if that is happening across your entire closet, there’s a good chance it’s time to revisit your style and how you want to look. 

Our member Amanda summed it up perfectly in that thread when she said, I stopped wanting to wear the colorful clothes I loved just a few seasons before. Being that bold didn’t feel right anymore and frankly, I’m just bolded out. Elegant and effortless feel like they suit me better now. I could not have said it better myself. 

If the things that you love just don’t do it for you anymore, chances are it’s time to reinvent your style. 

The third sign that your style might need a tweak, we’ll say, and this is probably the biggest one, is that nothing is wrong with your wardrobe, but nothing’s really right either. We talk a lot about solving the right wardrobe problem because if you solve the wrong one, you’re just wasting time and money and closet space. And honestly, I would not go to changing your personal style as the first solution. The first thing I would look at is the quantity and the quality of your clothes. Meaning, do you have the right clothes in the right amounts for the way you really live? That is where I would go first. 

I’m linking to my episode on building a ready-for-anything wardrobe in the show notes. I think it’s episode 236. You can learn more about what I’m talking about. That has been one of our most popular episodes ever, and I think it helps explain a lot of this. So if you haven’t, go check that one out. So that’s where I would look first. Does your wardrobe align with your life? 

But the other thing I would look at is the fit and condition of your clothes. I don’t care what you want your style to be. If your clothes are shabby and ill-fitting, it is not going to come together. But if you can get dressed easily and appropriately for the majority of your life, and if your clothes fit well and are in good condition, but you’re still like, I don’t know, I just need something. What you might be missing is personal style that speaks to who you are now. 

If you find yourself identifying with these signs – that you’re working too hard for your desired style, the looks you loved no longer light you up, and there’s nothing wrong with your wardrobe except an undefinable desire for something different – it might very well be time to give your personal style an upgrade or an overhaul. But before you hit the stores and have the expensive, difficult closet makeover I talked about in the last episode, hold up. There are a few big mistakes I see women make when they want to overhaul their style, and I want to make sure that you avoid those. So here are just a few. 

First one is confusing better style with different style. This has nothing to do with the good style we talked about earlier. So many types of style in this episode, I know. But this is not about whether your clothes are flattering or use good design principles. We are still talking about the personal style side here.

What I mean by better style is that sometimes the issue isn’t that your well-developed personal style doesn’t suit you anymore. The issue is that your personal style hasn’t been well-developed in the first place. 

Let me give you an example. In our Signature Style class, we teach members how to define their style by choosing three words that describe how they want to look. We call them style guideposts because they literally point the way to get to your desired style. My style guideposts are current, polished, and fun. T

hat’s how I want to look, how I want to be perceived, all that good stuff. If I don’t put any fun into my wardrobe, I am not going to look fun. And if I don’t do that, but I still have this idea that my style is current, polished and fun, I’m going to get dressed every day and go, oh, boring. I don’t like it. My words don’t suit me anymore. Better pick new ones. Well, maybe, or maybe it’s that my wardrobe is lacking in fun because all I put in there are things that aren’t necessarily fun. That’s obviously not true. You will have to pry my colorful pants off of my cold dead legs someday, but you get what I’m saying, right? 

Just because you want your style to be a certain way doesn’t mean it will be. You have to make it happen. You have to put the right things into your closet to get the right things out of it. So before assuming that your style doesn’t fit anymore, ask yourself if the issue could be solved by expressing your style more fully. I’m not saying that’s the case, but it is easier to lean in than it is to start over. 

The second mistake I see is trying to become someone you’re not. And this one happens in a couple of ways. And the first one is that when we don’t know what our style is, when we haven’t really thought about it, we see all great style as the right answer. And one of the biggest wins I see in the community that I love so much is women who say they can now appreciate other people’s style without wanting it for themselves or feeling like they have to buy the pieces. It takes a really discerning eye to say, oh, I love that, but not for me. When you don’t know how you want to look, the shoulds creep in. I should wear that. I should be trendier, sexier, dressier, whatever. Or you’re easily swayed by single one-off pieces, not really realizing that they’re part of a bigger, more cohesive style. And yeah, you can buy that skirt or that top, but if the rest of your closet doesn’t support that style, it will fall flat. 

The other way women try to become someone they’re not is by going really, really far from where they are right now. And this is something that I saw all the time as a one-on-one stylist. I’ve talked about it before. But women saw the time we spent together as an opportunity for total reinvention, to build a wardrobe for a version of themselves that they wanted to be or thought they should be. And I think it’s great to have a style that’s a little bit aspirational. We all need goals.

But a complete 180 is a different story. Like if you have been shopping exclusively at Talbots for 20 years, please don’t go buy an entire wardrobe from Zara because you want to be fashion forward all of a sudden. You’re going to end up with an entire closet full of clothes that you’re like, I don’t know. Can I wear this? 

One thing I know for sure when it comes to personal style is that trying to be someone you’re not is hard and it doesn’t last. It feels performative or like you’re wearing a costume rather than just expressing who you are. And the farther you go from who you really are and where you are right now, the less likely your new style is to stick. 

The last mistake I see women make when it comes to reinventing their style is not understanding the difference between definition and expression. I mentioned how much I love the thread in the community about changing personal style, but something I saw pop up in there a few times was women saying they changed their personal style when their lifestyle changed. And no matter how much I talk about this, something women really struggle with is the idea that your personal style is about who you are and what you want to express, not the situation you’re in.

Again, my style is current, fun, and polished. That is the definition of my style and what I want to say about myself through my clothes. But the expression of my style changes depending on where I’m going, what I’m doing, the seasons, all that kind of thing. For example, fun in my gym clothes means bright, happy colors. Fun in my everyday clothes means olive floral jeans like I’m wearing today or wide legs with big cuffs. I even had a tan and brown zebra print suit. That was super fun.

The point is, regardless of what I’m doing, there are ways to bring fun to my wardrobe because it’s bringing me to it. What I see is women having one style for athleisure and one style for work clothes and one style for casual clothes. And when that happens, what you’re doing is basing your style on the clothes or the activity, not on you. 

Style is fun when you work to express yourself through clothing. I’m guessing you are largely the same person in all parts of your life, right? At least I hope you are. Yes, you might be more professional at work and more relaxed with your friends, but you’re still you. You just express yourself differently. It’s the same with your wardrobe. The more separate the parts of your wardrobe are from each other in terms of style, the less cohesive and mix and match your wardrobe becomes. And when they are all speaking the same language, which is your style, that’s your style language, they talk to each other better and it’s easier to use more of what you have to get more mileage out of your clothes and you need less. 

Okay, so let’s say you’ve identified it’s time for a personal style reimagining and you’re not going to make the mistakes we just talked about. Now what? How the heck do you go about doing it? 

First things first, you got to get your mind right. You need to get rid of the word should. Should is a personal style killer. You’ve got to give yourself permission to like what you like and until you’re ready to do that, your personal style will probably always feel a little bit flat and you’ll probably try to overcompensate with the good style part. 

After that, though, you need to define how you want to look, not how you want to feel, I’m talking about you, comfortable, or how you want your wardrobe to function, like mix and match or machine washable. Style is a looking word, so start with how you want to look. 

Defining how you want to look gives you an attainable goal. Imagine getting in your car and deciding you’re going to take a trip. You start driving, but you haven’t decided where you’re going. How do you know which direction to drive? How do you know what to pack? How do you know if you’re getting close? How do you even know when you arrive? This is what trying to have or change your personal style looks like without defining where you want to end up. Just saying, meh, I’ll know it when I see it is a really expensive, time-consuming, frustrating way to develop personal style. Defining your style gives you a destination and a roadmap to get you where you want to go. 

Once you’ve got that rough idea, try it out. Do not get stuck on defining your style. It is more important to spend time trying it out. Go to your closet and see if you can pull together fully developed, cohesive outfits that you like out of what you already have. The truth is, even if you’ve never ever thought about your style and you’ve just been collecting clothes along the route to nowhere, you should have some clothes that embody your style. If you go to your closet and your desired style is nowhere to be found, that is a really good sign that your desired style might not be aligned with who you are authentically.

We’ve already talked about my style, current, polished, and fun. And if I said today, nope, that’s not my style anymore. Today I’m changing my style to be romantic and feminine and soft. I could not pull that out of my closet. It’s not a style that resonates with me, even on a subconscious level. If you say your style is current, but you have no idea what’s current, you have no idea where to find what’s current, and you haven’t shopped in years, that’s probably a sign that current is aspirational, not necessarily who you are or wanna be right now. It doesn’t mean that you can’t work to put some current pieces into your wardrobe, but that might not be who you are style-wise right now. 

Also, go to a store, any store that sells clothes, and try things on that you think reflect the style that you wanna have. Push yourself a little bit and use your desired style as a lens to identify pieces to try. For example, if I say, oh, I want my wardrobe to be fun, I want my style to be fun, go looking with the fun lens, identify things that are fun and put them on your body. 

Something interesting happens when you try new things that are aligned with your natural style versus when you try new things that aren’t. When you go beyond your comfort zone, but it falls within a style that naturally resonates with you, there’s a feeling that, oh, okay, this is different, but I think I like it. Versus when something isn’t aligned with your natural style or who you are, that produces a feeling of inauthenticity, of putting on a costume or wondering what would people say? The feeling is just different. And once you experience what both of them feel like, you can start to use that as a tool to find things that hone your style, but still have a chance of getting worn. 

Finally, make the changes gradually. Like I talked about in the Death, Taxes, and Great Style  episode, there are some changes that come on you all at once, like going back into the office five days a week starting Monday, versus changes that don’t have that same sense of urgency. This is one of those. This challenge doesn’t need to be solved in a week or a month, and you will do yourself a disservice if you try to overhaul your style all at once. Slow change wins the day here. 

And the way I would approach this one is to give your closet just a quick audit first to identify the pieces that will help bring your style to life. Not every piece needs to or will perfectly embody your style, but it should help your wardrobe bring that style to life. For example, I have plain white t-shirts. Are they fun? Not overly, but I wear them with my fun jeans or under a fun jacket. Some pieces are just supporting players and that’s okay.

I want you to pay really close attention to your basics here. You’ve got to make sure that you have solid basics that reflect the style you want to have. If you want your new style to be edgier, but all of your jeans are medium wash straight legs, it’s going to be really hard to bring anything edgy into your closet and have it look right. You might need a more exaggerated leg, a darker wash, something, a jean that’s a little bit edgier, right?

A lot of women wanna start with the standout pieces thinking they will have the biggest impact, but it’s much better to start with the supporting players and the basics, nail those first. 

Then I want you to pull out anything that is clearly not your style. Like nothing about it looks the way you want to look. For example, if I owned a waterfall cardigan, which I don’t, I would take that out. It’s not current, it’s not polished, it’s not fun. And it won’t help me make outfits that are current, polished, and or fun. So that would have no place in my wardrobe. I don’t want you to get rid of anything yet until you really settle on a style that feels good. But for now, just move it to the back of your closet while you’re experimenting. It is so helpful to see what you’re actually working with and not get confused by closet noise. 

Finally, last step, add pieces that go all in. If you want your style to be a little bit bolder, don’t start with a farm real maxi dress. If you want your style to be more ladylike and refined, your first purchase probably should not be a Chanel blazer. Hold off on those over-the-top or investment pieces until you are sure that’s your style. There will be a time to really go all in, but it’s not first. 

Baby-stepping your way into a new style might take longer, but you’re gonna end up with a much better wardrobe, you’re going to make fewer shopping mistakes, and you’re gonna have a defined point of view that feels like you. And that is the point of personal style. 

Okay, here’s what I really want you to take away from this episode. 

First, your personal style is always evolving. It’s always changing. It’s changing as much as we are just day to day, year to year. This isn’t something that you can decide once and then never ever think about again. Your tastes will change. Everything will change and you might want to express yourself differently. When your wardrobe is functional, but it’s just not doing it for you anymore, it’s not lighting you up, it doesn’t feel like you, it might be time to reevaluate what your wardrobe is saying about you and whether or not that’s what you want it to say.

Also, I want you to keep this idea in mind that there are two sides to style, personal style and good technical style. Great style combines the two. So focus on learning what you can, but don’t forget to put yourself into your wardrobe because that’s what makes style fun. If it’s just about rules and getting it right, getting dressed can feel like a boring chore. And I don’t know about you, but my life has enough boring chores to do. I don’t need to start my day with one. 

Your homework for this episode is very easy. It’s very quick. You can do it right now. That is to spend five minutes, just five minutes, thinking about your style and what you want your wardrobe, your style to say about you. If you’ve already defined how you want to look, ask yourself if it still fits and whether or not you’re fully expressing it, or if there’s room to lean in a little bit. And if you’ve never thought about how you want to look, well, that sounds like a pretty good place to start and a good use of five minutes. 

That is all I’ve got for you today. Figuring out how you want to look and learning to bring that to life is one of the absolute best things you can do for your style. It saves you money, it makes getting dressed easy, and it helps you love the way you look, whether you’re going to the gym, running errands, or heading to the office. And that is exactly what we teach inside the Style Circle. So if you are ready to have great style, not good technical style, not personal style, but great style, we can help you get there. The link to join us is in the show notes. 

I will see you next time. And until then, remember that your everyday matters, so get dressed for it.