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Have you ever thought about what you think about style? Probably not. Most of us are on autopilot about our thoughts, but how you think and feel about style shows up in your wardrobe. So today we’re talking about where style really starts, and it’s not in your closet. Let’s get started


Hello, gorgeous. Welcome back to the everyday style school, the podcast that gives real lifestyle advice to real life women. If you’re new here, welcome. I’m your host, Jennifer Mackay, Mary. I’m a wardrobe stylist who’s been dressing everyday women for over 20 years. And I’m the founder of everyday style, where we are on a mission to inspire women to love the way they look and give you the tools to make getting dressed easy. If you’re a longtime listener, welcome back, I am always happy that you chose me again today.

About a year ago, I recorded an episode about the five habits of highly stylish women. And it’s become one of my most popular, most downloaded episodes. Everyone wants to know what the stylish women that we see and want to be are doing right. And I get it, it’s like, just tell me what to do. And I’ll do it, let’s not reinvent the style, we’ll just make it easy. And I think there’s a lot to be learned from what those stylish everyday women are doing, how they’re getting dressed, which is why I shared that with you. But great style doesn’t start there. It doesn’t start with a great morning routine, or a closet full of clothes that are perfect for you. It doesn’t even start in a store, or a box delivered from Stitch Fix. Better style starts in your head, which is what we’re talking about today.

This episode is for those of you who’ve been listening for a while, and maybe you’ve been saying to yourself that you want better style. But for some reason, you just can’t make yourself do it. You can’t face a shopping trip, even an online one, the thought of planning your outfits for a week seems like a good idea. But maybe next week, you really want to be that stylish woman at the park or the office or the grocery store. But you just for some reason can’t get there. One thing I learned when I was working with clients One on One was that what was in their heads was really more important than what was in their closets. So today I’m going to share four things stylish women believe or think either way, it’s four little mindset shifts, that will help you get to the place where planning your outfits seems like a better use of 10 minutes, then scrolling Instagram some more, or buying that dress, it’s a little more out there for you is more exciting than it is scary. But there’s another group of you this episode is for two. There’s a meme that I see every now and then usually on Instagram. But it says, quote, I either dress like I’m going to a red carpet event or like I’m homeless, there is no in between, and quote, now, I’m not disparaging the unhoused. That’s literally the meme I saw. And perhaps you’ve seen that one, or some variation of it.

Regardless, this is about style consistency. And what I find is that if this describes you, there’s a good chance that you look at style as something you do when you have to, or when there’s a reason to, it’s not really a part of who you are or what you value. And it certainly isn’t easy. Maybe it’s not a daily practice or habit that you just do. And sure we all have our days when we don’t want to run into people we know at the store, myself included, I have those days. But when there’s such a huge disparity, I have to wonder if changing your mind about style might narrow the gap between the red carpet days and you know, the other days. So let’s just jump in. The first thing that stylish women believe is that whatever they like is valid. As I often say, you have to give yourself permission to like what you like, who cares if Julie down the street likes your dress or not? Who cares if Karen at the office thinks your shoes are ugly, until you give yourself permission to like what you like and believe that your tastes and opinions are completely valid. Style is going to be a struggle, and likely your wardrobe is going to be a little dull, a little drab. If every time you shop or you get dressed you have the thought of Oh What will people think you’re going to gravitate towards things no one would have any strong opinions about this leads to safe, probably a little boring, probably not the thing you wanted to choose choices every single time. When you see a stylish woman you probably noticed the standout pieces, the unexpected accessories, the pattern or texture mixing something something to grab your eye and You know, I know trying new things can be scary. I know we all worry about what people think sometimes, if you do, you’re human, you’re not weak. Every style website out there, probably including mine somehow talks about confidence. And that’s great. I think your clothes should give you confidence. But how do you actually get confidence? How do you get to the point where you don’t care what other people think. And I want to share something I heard recently, that’s had a huge impact on me, and hopefully it will for you, too. This was in a book I’m listening to about goal setting. But I think it really applies to pretty much everything in life. The author was talking about setting big goals, like kind of big, scary stretch goals. And two things people expect to have in order to reach those goals is capabilities and confidence. First, he dispelled the idea of the capability saying, if you had the capability to reach a really big goal, you probably would have done it already. Right? Good point. Then he talked about confidence. And she said that confidence comes from mastery from doing the thing and getting better at it, then you feel confident. Instead, he said, In the beginning, you need courage, you need to acknowledge that it’s weird or awkward or scary, or that you’re worried what people will think, and then do it anyway. That’s courage. In his style perspective, what you’re going to realize is that Julie down the street actually love that dress, or that Karen complimented your shoes. Or you might find more likely that neither of them really cared either way. And it was a total non issue. And when you have like a neutral reaction or a positive reaction, that little step gives you a tiny bit of confidence to do it again next time, and the next to the next. And all of a sudden, you’re buying clothes and getting dressed without even thinking about Julie or Karen. So don’t rely on style, confidence, try on style, Courage instead. The second thing stylish women believe is that style matters. If you’re still listening to this show, thinking what you wear doesn’t matter. First of all, why why there are so many other shows dedicated to the things you do believe matter. So go invest your time there. Or the other option is to actually admit that you believe that what you wear matters. Now, I want to be really clear that I think we should put style in our wardrobes. In perspective, I don’t think a great outfit is more important than being timed. I don’t believe you should skip out on invitations and opportunities to engage with life, because you don’t feel like you have the perfect outfit. Not at all. Life is more important than style. But if you’re honest with yourself, you’ll admit that when you like the way you look, you carry yourself differently. You walk a little taller, you smile at people more, you might even have more patience with your children. There’s a meme about that one too, which I love. Because it’s true. And this is where the confidence comes in. Because when you’ve got on a great outfit, and you feel great, you’re more confident in everything you do. I’m going to be really blunt for a minute and tell you about my interactions over the years, with women who have told me that what they wear doesn’t matter. They came in two groups. The first was perfectly happy women who were more often than not into gardening and the outdoors, et cetera, et cetera, et cetera, right? When I spoke to women’s groups, these women didn’t come up to me and say anything, they were polite and lovely. And if I found myself in a conversation with them, they would mention that they weren’t really into style. But, you know, it was obvious that my mere presence wasn’t offensive to them. I just wasn’t their person. It just wasn’t their topic. And that’s perfectly okay. The other group though, these women were not happy. They were the angriest, most hostile women I have ever come across. When I was on stage, they would be shooting daggers at me with their eyes. And as soon as I was done, they would make a beeline over to me to tell me that they didn’t care about style, and that what they wore didn’t matter. Friends, do you know how many topics I don’t care about? Infinity. I don’t care about an infinity number of things. You know how many speakers I have actively sought out to tell them that I didn’t care. Zero. When you don’t care. You just don’t care. In the words of Queen Gertrude from Hamlet. The lady doth protest too much, methinks. Now out of those two groups of non style caring women, not a single one from the first group ever hired me I never heard from them again. That’s fine. The second group though, they were an amazing source of clients. It took a few months sometimes it took a few years, but I would get an email saying I need your help. and they would spend our first hour together telling me how much style didn’t matter. And I would just smile, handing them item after item to try on like, okay, Linda, I believe you sure, whatever. Over the course of our time together, they would melt a little bit, they got a little bit friendlier, they started to smile. And by the end, most of them admitted, style mattered, and they felt better.


I know I’ve said this before, but sometimes we have this idea that believing style or what we wear matters makes us silly or frivolous. And I promise you, it doesn’t. You can look at yourself in the mirror and say, dang, I look good today, and still be a good person. So if you’re in that what I wear doesn’t matter camp, try saying the opposite to yourself for a week or two, just you might find your feelings changing, it’s okay to admit that you’d like to look good. Alright, belief number three. And honestly, it’s fun probably should have been first, but I’m too lazy to go back and change it. So it is what it is. And this is that stylish women believe they’re worth it. You Yes, you, you deserve good jeans. You Yes, you deserve to feel good about the way you look. The reality is that if you’re at the beginning of a style journey, it can be a little bit difficult, you have to put in a little more time, a little more effort and a little bit more money to get your wardrobe to the place where style is easy. And all of that time, that effort that money, all of those resources have to come from somewhere. You know, I’ve never been a stylist for the ladies who lunch crowd, right? I’ve always worked with moms or working women or working moms, you know, busy women who had plenty of other things that they could have put before themselves if they chose to. And if you are subconsciously nodding right now, girl ICU, I get it. But if you want better style, you have to believe that you’re worth spending those precious resources on sometimes at the expense of other people. Again, not seeing your family should be in shoes that are falling apart. So you can have a new Gucci bag. But I know a lot of women whose kids are dressing way, way better than they are. Maybe it’s time for a little resource redistribution to put yourself in the mix. And sometimes push yourself to the top of the pyramid. You know, it’s funny, women always expressed guilt for spending the time or money it took to work with me or to buy the new clothes. But I have to tell you, almost every husband I met was so supportive, like just do whatever it takes to feel good. They were they were glad I was there. And maybe I just got lucky to meet the good ones. But I truly do believe that most of our people, our spouses, partners, heck, even our kids wouldn’t bat an eye at spending some time, money or effort on ourselves actually think they want that for us. We’re the ones who tell ourselves that we should go last. So if you’re putting everyone else ahead of you, try telling yourself that you are worth the investment. Alright, the last one I want to share with you today is that stylish women believe you can learn to be stylish. One thing I’ve noticed over the years is how many women apologize to me for not knowing things. Like, oh, I’m sorry, I didn’t know this. But or I feel like I should already know this. But I feel silly for asking this. But what this tells me is that we haven’t quite given up the myth. That style is an innate trait you were either born with or not. And this belief is so so damaging. I want to share a conversation that I had a couple months ago in real life. I was at a kid event talking to other moms. And we were talking about what I do for a living and style in general. And one of the moms said, I wish I could learn to do that. And I laughed and I was like, well, you can in fact, I might know someone I wasn’t trying to sell her stuff. I never ever, ever do that to people in my real life. But she just said she wish she could learn to do exactly what I teach women to do. So you know, two and two together. Then she said something really curious to me, which was, but I feel like that’s cheating. If I have to learn how to do it. I’m not really stylish, you know? And I was like, wait, what? She said she wishes she just knew how to put things together. That in her mind would mean that she had real style trends. If I take a cooking class and it makes me a better cook, I’m still a better cook. I’m not a fraud because someone had to teach me how to make a fancy sauce. If I take a course on how to speak French, I still know how to speak French. I’m not an impostor because the spirit of the French language wasn’t bestowed upon me. style and dressing your Self are largely the same thing. There’s color theory to be learned and proportion, and a whole vocabulary that might be foreign to you. Some people get there by years of trial and error. Some people learn from a book or a class, or some woman on the internet some way, one way or another, you learn. And I actually compare this to cooking a lot. There are some really talented chefs, right. And then there are great home cooks, then there are people like me who have to get dinner on the table a few nights a week. And I prefer that it actually tastes good. So I have learned to become a better cook. Those really super talented chefs and home cooks, they probably started with an interest in cooking, and food. Everyone seems to be born with an interest in something. But even those people, even when you’re born with an interest in something, then you learn, you know, my brother in law, he’s a great cook, he loves to cook. And he’s always watching shows about cooking and trying new techniques and new gadgets. I don’t do that. I don’t have the same inherent passion. But I’m a really decent weeknight Cook, because I learned it’s the same with style. The gentle lions and Rachel Zoes of the world were born with an interest. And then they learned, you may never be gentle lions, I’ll never be gentle lions, you may never be a style visionary. But you can learn to put a great outfit together and to build a wardrobe. I was always surprised by how many of my clients, usually the ones on the more stylish side had already invested in their style educations. They had taken classes on colors, they’d read books about styles, they had bloggers they followed. In fact, working with me wasn’t an admission that they didn’t know what they were doing. It was just another part of their style education. And they brought what they already knew, to our sessions, which was always really fun for me. So never apologize for not knowing something. Movies and pop culture might make us think that every woman came out of the womb, knowing how to get dressed and ready to go shopping. But that is not the case at all. No one teaches you this stuff. Don’t believe that because you don’t know. It can’t be done. You can learn color theory, you can learn proportions, you can learn to put outfits together, and there’s no shame in that at all. You are still more stylish, even if you had to learn how to do it. Alright, that’s all I have for you today. I hope today’s episode makes you think about what you think about style. Because better style starts in your head, not in your closet. I will see you next time and remember your everyday matters. So get dressed for it. And that’s a wrap. Thank you for listening today.

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