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You've heard me say it before. Style is a skill and dressing well is a habit. And while that might sound simple, it doesn't mean it's always easy. Building habits can be hard. It takes practice, intention, and consistency. And those things can be difficult when you're just trying to live your life. You've got work to do and errands to run. Putting together a cute outfit just to go to Costco can seem kind of pointless. But if you want better style every day, you've got to create the habit of everyday style. And that's what we're talking about, about today. So 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 Mackie. Mary, after 25 years of dressing women with real bodies, real budgets, real 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. If you remember back a few months ago, we started this season talking about the habit of dressing well. And I talked about a really important element when it comes to getting habits to stick, and that is to discover why you want the habit in the first place. The truth is, if a habit isn't meaningful to you, if there's no reason to do it, or you're not getting anything out of it, you're not going to stick with it long term. But knowing your reason for or the benefit of the habit is just the start. After you've established that you have to do the thing with enough frequency and consistency to actually turn the action into a habit. For example, you probably don't need a habit of getting dressed for white tie events. For the vast majority of women listening to this show, it's not a common occurrence. It would be hard to do that with enough frequency and consistency for it to become second nature. So it's okay if it throws you for a loop once every five years, 10 years, or if you are like me, once every 25 years. On the other hand, there's an opportunity to practice everyday style with frequency and with consistency. Because you can literally do it every day. It's in the name right before we get to how to make dressing well every day a no brainer automatic habit. Let's talk for a second about everyday style and what it really means. There are two parts to everyday style. We're going to break them down. There's everyday. Guess what the other one is. And there's style. So let's talk about what they mean and how they work together. My definition of everyday is the stuff in your life you don't necessarily have to dress up for. For me, that includes things like working from home, running errands, hanging out with my sister or my daughters, walking my dogs, that kind of thing. For someone else. It could also include a casual workplace if it has a strict dress code or you feel like you need to or want to put in lots of extra effort. That's not that everyday life. To me, for example, grabbing dinner with my husband after buying mulch because both of our kids are out and neither of us feels like cooking. That's part of my everyday. But going to a nice dinner to celebrate our anniversary would not be under the everyday umbrella. That one I do want to put more effort into. Does that make sense? Good. Now let's talk about style and how it applies to the everyday. I'm not going to tell you what style is. We've talked a lot about that. And besides, your style doesn't have to be the same as mine. Your taste doesn't have to be the same as mine. Style is personal. But everyday style is different than just getting dressed every day. It's getting dressed for your everyday life and liking the results. It's feeling good, feeling put together, and not feeling embarrassed when you run into someone you know while you're just out and about living your life. The problem comes when we approach these words like they have no relationship to each other, but we pretend like we're putting them together when really we're not. Let me explain. It's like you understand on one hand what your everyday is and you also on the other hand understand what style is. So you think that together they make everyday style. But in your head, deep down somewhere, you're still saying, well, there's my everyday life and then there are times that I want to be stylish and they're still lacking that critical integration. This is a really important point because here's what I know and you can correct me if I'm wrong, but I've been doing this long enough to know that I am not we, meaning the well intentioned style advice givers of the Internet often talk about struggling to get dressed. I know I do, I know I have and there is truth to that. But the reality is you are probably not struggling to get dressed for your everyday life. In fact, I would be willing to bet you did not spend 20 minutes this morning deciding what to wear, doing the little flamingo move to see what you look vest, trying on outfit after outfit. Not if you were listening to this episode on an average regular day anyway. Those are the kinds of things we do for special occasions or when we feel like it matters more. It probably took you less than 5 minutes to pick an outfit this morning. It wasn't stressful, it wasn't difficult, but it was probably just underwhelming. It didn't leave you feeling good about yourself or stylish. And so the chances are your issue isn't that you can't get dressed, it's just that you don't love the result. And you might even spend a good chunk of that everyday life feeling blah or feeling frumpy, wishing that you felt good, wishing that you felt stylish, wishing you weren't embarrassed when you see someone you know at the store. So everyday style isn't style you have every day, the two word every day meaning each day. Everyday style is style you have in the everyday. That one word every day meaning that regular, average life stuff where what you wear really, truly only matters because it makes you feel good, because you dread the grocery store less when you have a good outfit on because your friend says, oh, you look so cute when you run into each other while walking your dogs. That is what we're talking about with everyday style. And the truth is, this is a longer conversation for another day. But everyday style is actually the hardest kind of style. It goes against everything we've been taught to think and do when it comes to style. But everyday style, in my completely unbiased opinion, is the most important kind of style. Because I believe you should feel the best in the chunks of your life where you spend the most time. And for a lot of women, especially as the world gets more casual women, the majority of life is spent in the everyday. So the philosophy that you should just frump around and feel bad until it quote, unquote matters will never make sense to me. Never. But even though I think everyday style is vitally important to living a full, rich, joyful life, I can still admit that spending a ton of time figuring out what you're going to wear to run errands can feel a little unnecessary. And I know a lot of women feel that way too. And sometimes it feels like we only have two choices. Lots of effort and good results or little effort, underwhelming results. But that is not true. That is not even close. You just have to understand how to put your everyday style on autopilot so that it's not this extra thing you have to do when you're just trying to live your life. And the best way to do that is to make it a habit. So let's talk about how to do that. The first thing you need to do is redefine what style means to you. This might not be something you ever thought about consciously, but we all have an idea of what style really looks like to us. Again, it's subjective. In the Style Circle, one of the first classes we encourage our members to take is Signature Style, which helps you define how you want to look and gives you a style roadmap. My style, I know I've shared this before is current, polished and fun. That's it. That's how I want to look. That is style to me. Notice there is nothing in my definition of style about needing to wear four accessories or always adding a third piece or wearing heels. I just want to look current, polished and fun. If I hit that, I have reached my definition of style. So last week we released our newest workshop to our members and it is all about how to use more color in your wardrobe without looking like you got dressed in the dark. The next morning I posted my gym outfit of the Day inside of our community and I was showing one of the color pairing formulas from the class that we talked about in action. Now, I didn't accessorize to go lift weights and I certainly wasn't dressed up, but I did hit my definition of style. My outfit was current, polished and fun. Mission accomplished. I don't post a lot of photos of my outfits because in reality they're often not over the top, identifiably stylish, or style inspo. They're just me living my everyday life in clothes I feel good in. A lot of our Style Circle members put more effort into their outfits than I do. Truthfully, some days, especially when I'm going somewhere special, I do put in extra effort. I accessorize. I I think a lot about my outerwear. I love outerwear. But my everyday often involves going nowhere and from where I am sitting right now at my desk, I can spy with my little eye at least five pieces of jewelry that I have put on and then removed because the bracelet was banging on the keyboard or the necklace was in the way during a podcast. Recording that kind of stuff for me isn't always practical, but every single day I feel stylish because I have fulfilled myself my definition of what style is to me. So my question to you is, what do you think style really is? Are you still conflating dressing well with dressing up? And if you don't have to dress up that often. What does that mean for what you wear? Is there a huge difference between outside you and inside you? Really going places Jen isn't any more stylish than stay at home Jen. She just wears some jewelry and a fabulous jacket. That's it. How my style is expressed changes depending on where I'm going or what I'm doing. But at its core, how I define style is the same. The bigger the difference between how you approach style when people see you versus when they don't, or when it matters versus when it doesn't, the more likely it is that style is an act you're performing for others, not a habit you're doing for yourself. And just a quick side note to my to my style circle members, this is why I keep harping on the fact that you need to be able to apply your words to both pajamas and a formal outfit. If you can't, you're probably still focused on the expression, not the definition. I could have current polished fun pajamas. I do, in fact. And I could also have a current polished and fun ball gown. I do not. But the definition is the same, just the expression of it changes. Recently, someone told me that she had taken a break from style, and I'm going to come back to this idea later. But I think it's important here too, because what this tells me is that to her style is this extra thing. It's a thing that requires work and effort and thinking, and when that's the case, it's easy to take a break from it when things get in the way or when it isn't practical. It makes me wonder what style meant to her and if it was more focused on expression rather than just definition. I have a feeling that's the case now. Once you understand what your definition of style is, you still got to do the thing. Something I mentioned earlier is the importance of doing the thing with enough frequency and consistency for it to become a habit. These are different aspects of habit formation, but they work together as well. Frequency. That one's easy. Frequency is, how often do I do this? For something like picking an outfit for your Christmas party, the answer is like once a year. And it's pretty much scientifically impossible to build a habit of doing something that happens once a year because it just never gets traction. So if you think of dressing well as something you only do when it matters and it doesn't matter all that often, it'll be difficult to get the traction you need to get good at it and not think so much about it. Frequency determines how Fast you develop a habit. That one's pretty straightforward. Consistency is a little tougher. Consistency answers the question, how reliably do I do this? So let's say you get dressed for that everyday part of life five days each week. Out of those five days, how many days do you practice everyday style? Which, remember, is different than just getting dressed. It's getting dressed and liking the results. If you do that once a month, you are practicing everyday style 5% of the time. Once a week, 20%, four times a week, 80%. By the way, I had to use my calculator for that and I'm not proud. But what's important here is that consistency determines the permanence or the stickiness of the habit because it controls the identity shift required for lasting change. It takes you from a person who puts on a stylish outfit to a stylish person. Dressing well, no matter what they're doing or where they're going, is just what stylish people do. There are four ways frequency and consistency can work together when it comes to dressing well. Ready. Number one is low frequency, low consistency. This is scientifically called random effort, and it's what women do. When you only try to dress well for the rare, important it matters event. This is not going to become a habit and dressing well will always feel hard. Number two, we've got low frequency, high consistency. So let's say you decide that you are going to dress well every Friday. Doesn't matter what you're doing, you're going to look good doing it. This will actually build a habit. And that habit might bleed into wanting to dress well on Thursdays too. Who knows? Sky's the limit. But the drawback to this approach is that it takes a long time because it's low frequency. Right. And it's going to feel awkward longer, which is something that gets in the way of developing habits. We often don't stick with things long enough for them to feel automatic because it feels strange until it doesn't feel like anything at all. So we never get to that point where you're like, oh, I didn't have to check my outfit against my style words and I just did it anyway, right? It, it takes longer for it to become automatic and we just kind of lose momentum in that awkward phase. Number three, we've got high frequency, low consistency. So let's say tomorrow you decide you want better style. It matters to you. You are going to reinvent yourself. So every single day for the next two weeks, you dress to the nines. You never leave the house without a fabulous outfit and a full face of makeup on. Often. What happens here is that the burst of motivation that got you going doesn't last past the fun part, the new part, which we're going to talk about later, and you burn out so it doesn't turn into a lasting habit. The last one is high frequency, high consistency. And this is the magic formula to make everyday style a habit. Any habit really, very, very quickly. Dressing well becomes a habit that you just automatically do. You stop trying to dress well and you just become a person who dresses well because you've got the frequency speeding up the time and the consistency to make the habit sticky. Now, what I see a lot of women getting tripped up by is the difference between consistency and perfection. Those two things are not the same. And this is when the belief that good style can only mean dressed up, fully accessorized outfit with pretty but impractical shoes, that idea is going to come back to bite you in the butt. If that's what you think good style means, only right. If that is your definition of style perfection, fine. But if your lifestyle or your personal style doesn't support that definition and you only do it when it matters, chances are good that you're going to be stuck in that low frequency, low consistency, random effort, vortex. And style, everyday style or otherwise, will never get easier or better that way. Everyday style consistency simply means making a little effort most days to like what you're wearing, regardless of what you're doing. That's it. You don't have to overthink it or over complicate it. So let's go back to motivation, which I briefly touched on. I am a big believer in motivation when it comes to everyday style. Like I said, we started this season talking about discovering your motivation for wanting better style. And I still think that's really important. I haven't changed my mind on that. It's like, why are you doing this? Why does it matter? On a macro level, understanding your motivation matters. It's kind of your North Star for anything. But on a micro level, when it comes to getting dressed on a daily basis, motivation isn't as effective in this case. What you need to rely on instead is momentum. And let me share a little story with you to demonstrate what I mean. A couple of years ago, I was a gym girly. I was dedicated, I was consistent. And even when it was 10 below zero outside and it was dark in the winter and my accountability partner texted me that she was bailing on our 5:30am meeting, I went anyway, like I was a gym girly now. Long story short, I had some health challenges that ended in a six day hospital stay in a major surgery, which psa, if you aren't due for a colonoscopy, just schedule it today. You're welcome. That. That's my good deed for the day. Anyway, I stopped going to the gym. First I didn't feel great, and then I literally couldn't. And then I just didn't want to. And then I wanted to, but I couldn't get started. Then I got in my head about not being able to get started. It was like this whole thing. Now, was I motivated to go to the gym? Like, did I have reasons for wanting to exercise? Yes, absolutely. The least important of which is that my formerly toned arms now have this like, weird squishy part that I don't love. I want it gone, right? So I was lamenting to my athlete daughter who goes to the gym all the time, that I needed to get back there and start working out again. So I said to her, we should go together. To which she replied, well, how about tomorrow morning? Huh? Tomorrow, huh? You mean like the next time I wake up that. That tomorrow? Because when I said we should go to the gym, I guess I meant abstractly that we should go do that sometime, someday, not 12 hours from now. And every fiber of my being wanted to say no. But the saying a journey of a thousand miles begins with a single step popped into my head. And I thought, you just gotta do the thing. You have to start somewhere whether you want to or not. Motivation assumes you're going to want to. And then I also thought, when your teenagers ask you to do things with them, you do it. Moms of younger kids, please write that one down. It's really good parenting advice. So I said yes, even though I was not motivated at all. We went the next day, and it was hard and it was awkward, but it also felt really, really, really good. And the next week I said, let's go twice. And we did. And then I started going on days that she couldn't so that I could get three days in. And before long, I stopped asking myself if I was going to go to the gym in the morning. And I started going, because that's what I do every other day during the week. It became a habit again. As long as I was relying on motivation alone, I nothing was getting done. I wanted Michelle Obama arms, but that was not enough to get me out of my comfy, cozy bed in the morning. It took momentum to get started. And what momentum gave Me was the opportunity for frequency and consistency that allowed me to bring back the habit. A lot of people rely on motivation to inspire momentum, when really it just doesn't work that way. The way I look at it, motivation and momentum are a loop. The momentum I got from even going a couple of times, feeling the muscles that I hadn't worked in over 18 months, they gave life to my motivation. It reminded me that all the things I want are possible and that I was working towards something. And when your motivation feels alive and achievable and even closer than you think, it feeds back into momentum to keep you going. And the thing about relying on motivation alone for daily action is that it fades. Motivation often burns really bright in the beginning, but it dims before the habit sets in. By the way, you know that idea that it takes 21 or even 30 days to make something a habit? Yeah, that's a myth. It actually takes between 18 and 254 days to make a habit stick, with an average of 66 days. Lots of factors determine how long it's going to take to make something a habit. But guess what influences that number? Yup, frequency and consistency are old friends. There is a psychological phenomenon called the fresh start effect that basically says people have increased motivation around time based landmarks. Things like New Year's, their birthdays, a new season, even Mondays. It's a marked shift in time that makes us feel like we're starting over with a clean slate. It's like January in the gym, right? New Year, new you, which I have always hated. But I even see this around the start of a new season in our membership. It's like the new season is an opportunity for reinvention or a fresh start. And that is wonderful. But a few weeks in, what you realize is that you're still the same. You, you still don't want to wear dresses to the dog park, you still prefer sneakers to heels. You've gone through all the fun outfits that you can think of and the motivation wears off. The high of doing something new wears off and the fact of, oh, if I want these results, I have to keep doing this every day sets in and that burst of energy you started with is over. Anything that is worth having long term needs to be approached like a marathon rather than a sprint. The fresh start effect is basically high frequency, low consistency in action, made worse by the fact that most people begin a fresh start sprint with perfection as a goal. Most people aren't like, this year I'm going to go to the gym once a week. Nope, it's this year I'm going to exercise every single day. And they do for like two weeks. But a habit has to be sustainable. That is way more important than getting it perfect. Perfection is exhausting and ultimately defeating. Now I want to wrap this up with a super duper practical way to make the habit of everyday style completely foolproof. Style really is part mindset, part practical action. You cannot have one without the other. And I talk a lot about the mindset part of it because it is the part we skip most often and it's what is holding women back the most. There's nothing you can buy that will overcome thinking that style doesn't matter or that you don't deserve nice things, or that you can't dress your body well. But the other side of that is that you can have the healthiest style mindset in the world. But if you don't have clothes, it doesn't matter either. Today I have given you plenty of the mindset stuff. So let's end with the practical. Did you know it is almost impossible for me not to look stylish every day? And I don't mean that in a oh, I'm just so stylish. I couldn't look bad if I tried. It just comes so naturally. No, that would be disgusting. And I wouldn't listen to me either. But that is not it at all. But the truth is, even if I wanted to, I could not go to my closet right now and put on an outfit that makes me feel frumpy or dated. Do you know why? Because I don't have those things in my closet. My definition of style, remember, is current, polished and fun. Right? If you went to my closet, that would literally be the only result you could pull out. You don't even have to think about it. It just happens. It's funny. Yesterday I was scrubbing my deck. I know I live a very glamorous life. Please don't be jealous of me. But I got home from a sporting event in the morning with one of my girls and I had already been outside with no shade for like five hours. And if you know me, you know I am part vampire. So to scrub my deck, I needed an outfit that would protect me from the sun. I that was my only style goal. I wore a baseball hat and a sun shirt and like UPF 50 pants. My husband came up the deck stairs from pulling weeds and he said, that's a really cute outfit. Now, was that my goal? No. But was it current, polished and fun? Yes, because that's all I own now, let's be really, really clear. I did not look ready to head to dinner or meet up with friends. I was sweaty. My hair was frizzy. I was a hot mess. But the point is, I was dressed appropriately for the task I was doing while still staying true to my style without any extra effort, because that's all I own. Remember the woman I told you about who said she'd taken a break from style? The rest of the story is that she told me that she had been sick, she hadn't been wearing real clothes, et cetera, et cetera. And I get it. I do. But here's the thing. I had also, when she told me this, I had also just been sick. And I had also not put in on real clothes in probably over a week. All I wore was loungewear and sweats. But guess what? My loungewear and sweats are. You got it. Current, polished, and fun. I don't have ratty leggings or stained sweatshirts. I don't own comfortable clothes that are way too big and make me feel frumpy and dumpy. I did not give up an ounce of comfort when I was sick. I was not laying in bed watching Netflix in some rigid denim jeans and a blouse. But I still felt pulled together and even a little stylish because I have stylish things for all parts of my life. I would bet my house that there are women listening to this right now, trying to pull something out of their closets that doesn't exist inside of it. And do you know why I can be so confident in that? I really like my house. I don't want to give it to you, but I have seen this countless times when I would do closet edits with clients after she got done trying on all the clothes. We would make outfits in the time that we had left together. And so many women had this idea that just because I was there, I would be able to make current, flattering, stylish outfits for them. But if they didn't have current, flattering, stylish pieces, that was not going to happen, because there is nothing magical about my presence. Whatever your closet is full of is the result you're going to get. The only result from my closet is current polished and fun. That's it. And this makes getting the style I want, no matter what I'm doing, so dang easy. I literally cannot mess it up. Now, I am not saying that you need to go have a closet bonfire and start from scratch, but I do think it's worth asking yourself if you have the Right things to to easily get the results you want. If you don't, you might want to consider doing some editing or adding. And when you add, you might have to consciously fight the inner voice telling you that dressing well means dressing up. You have to have clothes that you want to reach for for your everyday life. Otherwise you're just going to fill your closet with more stuff you don't want to wear for the way you really live. When I used to shop with clients, this was a phenomenon that I saw over and over and over. Working with me was kind of the ultimate fresh start. It was a time for reinvention. And at that time, I was working with a lot of women who were coming out of the baby slash little kid years and they were wanting to put themselves back together. And I love that. But I cannot tell you how many women who had been living in like ratty lightnings and lularoe tunics. I had to talk out of buying things like dress pants and blazers for their everyday stay at home mom lives. They were all like, yes, I would wear this to a play date. And I would say, ma', am, when was the last time you wore pants with an actual button and zipper? And then they were all like, oh, never mind. But I didn't want them just to go home in clothes that were beautiful but wouldn't get worn. So instead we put them in cute knit tops that they could machine wash. We put them in easy joggers jeans with stretch practical things that were still stylish and made them look and feel good. And here's the kicker that they actually wanted to reach for, because you can have a fabulous wardrobe, but if you don't want to wear it, what's the point? There was a woman in a challenge that I did a couple of years ago, and she was really stuck on this idea that dressing well meant dressing up. And she kept saying, but I just wear jeans and sweatshirts all the time. I just wear jeans and sweatshirt. And finally I said, well, okay, but you don't have to wear bad jeans and sweatshirts. That's the problem. Not that you're wearing jeans and sweatshirts. I live in jeans and sweatshirts. You guys already know this. And do you know what they are? Say it with me, friends. They are current, polished and fun. And frankly, they are pretty darn stylish. If you want effortless everyday style, the absolute easiest way to get there is by by creating a wardrobe that gives you the results you want without having to think about it or struggle for it. When you have that the habit becomes easy. Okay, your homework for this episode is to do the first thing we talked about today and the last. First, think about what style really means to you. Are you focused on how you define style or how you express style? Be honest with yourself and look for things in your definition that aren't realistic for everyday life. Then head to your closet and see how easy it would be to pull your ideal style out in an everyday way. If you don't wear heels regularly, don't start saying, well, you know what? I guess I could wear these because, yeah, you could, but also, no, you won't. If your everyday life is sneakers, and do you have sneakers that reflect your style? If your everyday life is flats, do you have flats that reflect that style? Whatever you wear, whatever you like to wear, you should have everyday versions that create everyday style. That is it for this episode of the Everyday Style School. Thank you for spending time with me today. If you are finally ready to make style simple, come take my free workshop where I will break down the simple steps that will help you stop filling your closet with clothes that don't give you the style you want and start making style truly effortless for life. We've got a workshop, a live workshop coming up soon, so head to freestyleclass.com or just click the link in the show notes. I will see you next time. And until then, remember your everyday matters. So get dressed for it. Sam.
The Everyday Style School
Host: Jennifer Mackey Mary
Episode: Everyday Style, Every Day
Date: May 12, 2026
In this episode, Jennifer Mackey Mary delves into the concept of "everyday style"—what it truly means, why it matters, and how to make dressing well into an effortless daily habit. Jennifer draws on her 25 years of experience advising real women and provides a practical guide to redefining style, integrating it into everyday life, and making it sustainable. Key themes include the difference between motivation and momentum, building habits through consistency and frequency, and making your wardrobe reflect your personal style at all times, not just for special occasions.
Definition of 'Everyday':
Definition of 'Style':
Integration of Both:
Many women equate dressing well with dressing up, creating a divide between how they present themselves when it “matters” and in regular life.
Jennifer’s own definition is “current, polished, and fun”—and this standard applies whether she’s in pajamas or preparing for a formal event.
Motivation vs. Momentum:
Frequency = How Often You Do It
Consistency = How Reliably You Do It
Four Frequency/Consistency Patterns:
Consistency ≠ Perfection:
Jennifer stresses that daily motivation is unreliable; real progress comes from building momentum through action, not waiting to “feel ready.”
Example: Her story of returning to the gym after a break demonstrates that starting, even imperfectly, is what restarts momentum and re-establishes habit.
Fresh Start Effect:
Jennifer’s own closet only contains items that reflect her definition of style—making it almost impossible to dress in a way she dislikes.
It’s not about buying a glamorous wardrobe or starting from scratch, but about editing what you have so you're set up for success every day.
"Whatever your closet is full of is the result you're going to get. The only result from my closet is current polished and fun. That's it." (57:47)
Avoid filling your closet with items you think you should wear for a fantasy version of your life; shop for how you really live.
For more insights and actionable tips, Jennifer invites listeners to join her upcoming free workshop (details in show notes). As she reminds us:
"Your everyday matters. So get dressed for it."