Jennifer Mackey-Mary: 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 today. 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! 

If you remember back a few months ago, we started out 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’s 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 do 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, that’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 ok if it throws you for a loop once every 5 years, or if you’re like me, once every 25 years. On the other hand, there’s an opportunity to practice everyday style with frequency and consistency, because you can literally do it every day. It's in the name.

Before we get to how to make dressing well everyday 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. There’s EVERYDAY, and STYLE–let’s break them down. Starting with Everyday

My definition of everyday is the stuff in your life you don’t necessarily have to dress up for. For me, that includes working from home, running errands, hanging out at my sister’s house, coffee dates with my daughters, walking my dogs–that kind of thing. For someone else, it could 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 everyday life to me. For example, grabbing dinner with my husband after buying mulch, because our kids are both out, and neither of us wants to cook is part of my everyday, but going to a nice dinner to celebrate our anniversary would not be under that everyday umbrella. That, 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 done that a lot, and besides, your taste doesn’t have to be 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. Feeling good, feeling put together, not feeling embarrassed when you run into someone you know while you’re out and about.

The problem comes when we approach these words like they have no relationship to each other and pretend we’re putting them together, when we’re really not. Like you understand what your everyday is, and you understand what style is, so you think that’s everyday style, but in your head you’re still saying–there’s my everyday life, and then there are times I want to be stylish–they’re still lacking that critical integration.

This is actually 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 I’m not. We–meaning the style advice givers of the internet–often talk about struggling to get dressed. I know I do. But the reality is, you’re probably NOT struggling to get dressed for your everyday life. In fact, I’d be willing to bet you didn’t spend 20 minutes this morning deciding what to wear, doing the flamingo to see which shoe looked best, trying on outfit after outfit.

Not if you’re listening to this on an average, regular day anyway. That’s the kind of thing 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…it was probably just underwhelming. It didn’t leave you feeling good about yourself. Chances are, your issue isn’t that you can’t get dressed, it’s that you don’t love the results. You might even spend a good chunk of your everyday life feeling frumpy or blah, wishing you felt good. 

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–one word, meaning the regular, average life stuff where what you wear really only matters because it makes you feel good. Because you dread the grocery store less, because your friend says “you look so cute” when you run into each other while walking your dogs. That’s what we’re talking about. 

The truth is, and 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. For a lot of women, the majority of life is spent in the everyday, so the philosophy that you should just frump around until it “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. It can seem like we have two choices– lots of effort, good results, or little effort, underwhelming results.

But that’s not true. Not even close. You just have to understand how to put your everyday style on autopilot, and the best way to do that is to make it a habit. So, let’s talk about it.

The first thing you need to do is redefine what style means to you. This might not be something you’ve ever thought about consciously, but we all have an idea of what style really looks like–to us. Its 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 is current, polished, and fun. That’s it. That’s how I want to look. Notice, there’s nothing in there about needing to wear 4 accessories, or always adding a third piece, or wearing heels. I just want to look current, polished and fun–if I hit that, I’ve reached my definition of style. 

Last week, we released our newest workshop to our members, and it’s 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 in our community, showing one of the color pairing formulas we talked about in action. Again, I don’t accessorize to go lift weights, and I certainly wasn’t dressed up, but I did fit my definition of style. It 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”. 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 put in extra effort, I do accessorize, I think a lot about my outerwear-I love outerwear, but my everyday often involves going nowhere, and from where I’m sitting right now, I spy with my little eye at least 5 pieces of jewelry that I’ve put on, and then removed because the bracelet was banging on my keyboard, the necklace was in the way during a podcast recording–that stuff isn’t always practical—but every single day I feel stylish, because I’ve fulfilled 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? 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? The reality is, going places Jen isn’t any more stylish than stay at home Jen–she just wears jewelry and a fabulous jacket. How my style is expressed changes depending on where I’m going or what I’m doing, but at its core, it’s the same. The bigger the difference between how you approach style when people see you vs when they don’t, or  when it “matters” vs 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. 

A quick note 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 pajamas and a formal outfit. If you can’t, you’re still focused on the expression, not the definition. I could have current, polished, and fun pajamas–I do, in fact. I could also have a current, polished and fun ballgown. The definition is the same, the expression changes.

Recently, someone told me she’d taken a break from style, and I’m going to come back to this later, but I think it’s important here, too because what this tells me is that to her, style is an extra thing–a thing that requires work, effort, thinking, and so 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 her definition of style was, and if it was more focused on expression than definition. I have a feeling that’s the case.

Once you understand what your definition of style is, you’ve still got to DO THE THING.

Something I mentioned earlier is the importance of doing something 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 is easy–frequency is how often do I do this? For picking an outfit for your Christmas party, the answer is once a year. It’s pretty much scientifically impossible to build a habit of doing something that happens once a year, because it 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 will be difficult to get the traction you need to get good at it, and not think about it so much. Frequency determines how fast you develop a habit. That’s pretty straightforward. 

Consistency is tougher. Consistency answers the question, how reliably do I do this? So, let’s say you get dressed for that everyday part of life 5 days a week. Out of those 5 days, how many 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 it’s 5% of the time. Once a week is 20%. 4 times a week is 80%. I had to use my calculator for that. I’m not proud. Anyway, what’s important here is that consistency determines the permanence of the habit, because it controls the identity shift required for lasting change. You go 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 4 scenarios of how frequency and consistency can work together in dressing well.

1- Low frequency, low consistency. This is what’s called “random effort”, and it’s what women do when you only try to dress well for the very rare important event. This is not going to become a habit, and dressing well will always feel hard.

2-Low frequency, high consistency–let’s say you decide that you’re 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 that might bleed into wanting to dress well on Thursdays, too. Who knows–the drawback is that this approach takes a long time, and it will feel awkward longer, which is something that gets in the way of developing habits. We often don’t stick with something long enough for it to feel automatic, because it feels strange until it doesn’t feel like anything at all–so we never get to the point where you’re like “oh, I didn’t have to check my outfit against my style words, and I just did it anyway”
3-High frequency-low consistency–Let’s say tomorrow you decide that you want better style, so every single day for the next two weeks you dress to the nines–you never leave the house without a fab outfit and a full face on. Often what happens is that the burst of motivation doesn’t last past the fun part–which we’re going to talk about later–and you burn out, so it doesn’t turn into a lasting habit. 
4- The last one is high frequency, high consistency- This is the magic formula to make everyday style a habit. Very quickly, dressing well becomes a habit you automatically do. You stop TRYING to dress well, and you become a person who just dresses well–because you’ve got the frequency speeding up the time, and the consistency to make the habit sticky.

Now, what I see women getting tripped up by is the difference between consistency and perfection. They are not the same. This is when the belief that good style only means dressed up, fully accessorized outfits with pretty but impractical shoes, is going to bite you in the butt. If that’s your definition of style perfection, fine, but if your lifestyle or your personal style doesn’t support that, and you only do that when it “matters” chances are good that you’re stuck in a low frequency, low consistency vortex, and style–everyday 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 all. You don’t have to over think. 

Let’s go back to motivation, which I briefly touched on. I’m a big believer in motivation when it comes to everyday style. We started this season talking about discovering your motivation for wanting better style, and I think it’s really important. Why are you doing this, why does it matter? On a macro level, understanding your motivation matters–it’s kind of your North Star. But on a micro level, when it comes to getting dressed on a daily basis, motivation isn’t as effective. Momentum is what you need to rely on instead.. Let me share a little story with you to demonstrate what I mean.

A couple of years ago, I was a gym girlie–I was dedicated, and consistent even when it was 10 below and dark in the winter, and my accountability partner texted me that she was bailing on our 5:30 am meeting, I went. Long story short, I had some health challenges, that culminated in a 6-day hospital stay and a major surgery–PSA, if you’re due for a colonoscopy, schedule it today. Anyway, I stopped going–I didn’t feel great, then I literally couldn’t, and then I just didn’t want to, and then I wanted to, but couldn’t get started–it was a whole thing. 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 weird squishy part I don’t love. 

Anyway, I was lamenting to my athlete daughter that I needed to get back to the gym, and I said “we should go together” to which she replied “how about tomorrow morning?” Tomorrow, huh? You mean like the next time I wake up? That tomorrow? Yeah, when I said we should go to the gym, I guess I meant abstractly we should do that some time. Someday. Not 12 hours from now. 

I 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 have to start somewhere, you just gotta do the thing-whether you want to or not. Motivation assumes you’re going to want to. And I also thought, when your teenagers ask you to do things with them, you do it. Moms of younger kids, write that one down. Its good advice. So, I said yes, even though I was not motivated at all.. We went the next day. And it was hard and awkward, but it also felt really really good. And the next week I said, let’s go 2 times, and we did. And then I started going on days she couldn’t, so I could get 3 days in. And before long, I stopped asking myself if I was going to go the gym in the morning, and I started going because that’s what I do every other day. It became a habit again. As long as I was relying on motivation alone, nothing was getting done–I wanted Michelle Obama arms, but that wasn’t enough to get me out of my comfy bed. It took momentum to get started, and what momentum gave me was the opportunity for frequency and consistency. 

A lot of people rely on motivation to inspire momentum, when really, it 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 I hadn’t worked in over 18 months–gave life to my motivation. It reminded me that all the things I want are possible, and that I was working toward something. And when the motivation feels alive, and achievable, and closer than you think, it feeds back into momentum to keep you going. 

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 real habits set in. By the way, the idea that it takes 21 or even 30 days to make something a habit is a myth. It takes between 18 and 254 days to make a habit stick with an average of 66 days. Lots of factors determine how long it takes, but guess what influences that number? Yep, frequency and consistency.

There’s a psychological phenomenon called the Fresh Start effect that basically says people have increased motivation around time-based landmarks like New Years, 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! 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’s great. 

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 you can think of, and the motivation wears off, the high of doing something new wears off, the fact that oh, if I want these results I have to keep doing this every day sets in, and the burst is over. 

Anything 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 exercise every day. And they do, for two weeks. A habit has to be sustainable. That’s way more important than getting it perfect. Perfection is exhausting and ultimately defeating.

I want to wrap this up with a super practical way to make the habit of everyday style completely fool-proof. Style really is part mindset, part practical action–you cannot have one without the other, I talk a lot about the mindset part of it because it’s the part we most often skip, it’s what’s holding women back the most…and there’s nothing you can buy that will overcome thinking style doesn’t matter, or you don’t deserve nice things. But the other side of that is that you can have the healthiest style mindset in the entire world, but if you don’t have clothes, it doesn’t matter either. 

Today, I’ve given you plenty of the mindset stuff, so let’s end with the practical. Did you know it’s almost impossible for me not to be stylish everyday? 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”. That is not it at all, but 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. You know why? I don’t have those things in my closet. My definition of style is current polished and fun, right? If you went to my closet, that would literally be the only result you could pull out. 

It’s funny, yesterday I was scrubbing my deck–I know, I live a very glamorous life, please don’t be jealous. I got home from a sports event with one of my girls, and I had already been outside with no shade for 5 hours or so–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. That was my only style goal. I wore a baseball hat, and a sun shirt, and UPF pants. My husband came up from pulling weeds, and said “that’s a really cute outfit”. Was that my goal? NO. But was it current, polished, and fun? Yes. Because that’s all I own. Now let’s be 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? She told me she’d been sick, she hadn’t been wearing real clothes, etcetera, etcetera. And I get it, but here’s the thing. I had also just been sick, and I hadn’t put on real clothes in probably 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. I didn’t give up an ounce of comfort when I was sick. I wasn’t laying in bed watching Netflix in some rigid 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. You know why I can be so confident? I’ve seen it countless times. When I would do closet edits, after my client and I got through trying all the clothes on, we’d make outfits in the remaining time, and so many women had this idea that just because I was there, I’d be able to make current, flattering, stylish outfits for them. But if they didn’t have current, flattering, stylish pieces, that wasn’t going to happen. There’s 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. Which makes getting the style I want–no matter what I’m doing–so dang easy. 

Now, I’m not saying you have to have a closet bonfire, and start from scratch, but I do think it’s worth asking yourself if you have the right things to EASILY get the results you want. If you don’t you might want to consider 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 you want to reach for your everyday life. Otherwise, you’re just filling your closet with more stuff you don’t want to wear. 
 When I used to shop with clients, this was a phenomenon I saw over and over. Working with me was the ultimate fresh start, and at that time, I was working with a lot of women who were coming out of the baby/little kid years, wanting to put themselves back together, and I cannot tell you how many women, who had been living in ratty leggings and LuLaRoe tunics I had to talk out of buying dress pants and blazers for their everyday, stay at home mom lives. They were all, “yeah, I want to wear those”, and I would say “when was the last time you wore pants with a button and a zipper”, and there were all “never mind”. So instead, we put them in cute knit tops, and easy joggers, and jeans with stretch–practical things that made them look and feel good–that they’d actually 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 I did a couple of years ago, and she was REALLY stuck on the idea that dressing well-meant dressing up, and she kept saying “but I just wear jeans and sweatshirts”, and finally I said, ok, but you don’t have to wear bad jeans and sweatshirts–THATs the problem, not that they were jeans and sweatshirts. I live in jeans and sweatshirts–and you know what they are? Say it with me–current, polished, and fun. And frankly, pretty darn stylish. 

If you want effortless, everyday style, the absolute easiest way to get there is 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.

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, I guess I could wear those”, because yeah, you could, but also no, you won’t. If your everyday life is sneakers, 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, you should have everyday versions that create everyday style. 

That’s it for this episode of the Everyday Style School. Thank you for spending time with me today. If you’re finally ready to make style Simple, come take my free workshop, where I’ll break down the simple steps to 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 coming up soon, so head to freestyleclass.com, or just click the link in the shownotes.

I’ll see you next time–and until then, remember, your everyday matters, so get dressed for it!