Jennifer Mackey-Mary: Despite everything you’ve done, does style still feel hard?

You’ve figured out your body shape, you’ve bought the “right” things, and maybe you’ve even listened to every episode of this show—but getting dressed still feels like a chore. You still struggle to know what to wear, and your outfits still feel underwhelming.

If it feels like maybe you just weren’t meant to have great style after all, you’re not alone—and you’re not bad at style. You just haven’t learned how to translate what you know into your everyday life so that style doesn’t feel difficult. This season is all about making everyday style easier by treating dressing well as a habit, not a special occasion.

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.

Well, hello Gorgeous! We’re back from our winter break, and I am so happy to be here. I’ve missed you! I hope you had a wonderful holiday season, and enjoyed some downtime to just rest and relax. For me, that’s what winter is all about. I took a major break in December and a good chunk of January–no socials, no emails–nothing. But that doesn’t mean I wasn’t working. In fact, quite the opposite. Having a little bit of breathing room just opened the floodgates of ideas, and things I wanted to create… and since we were last together, I created a brand-new free class that I’ll tell you about later, AND we added a new masterclass to the Style Circle, which I actually think is the most important class in the membership. It was a really good reminder that slowing down and taking a break isn’t a waste of time–sometimes it’s the most important thing you can do–and I’m just super energized and excited for all the things we’ve got coming up this year, so stay tuned.

Anyway, back to the present moment. Today, we’re kicking off our Spring semester, and a brand-new theme for the season.

One thing I say a lot is that style is a skill, and dressing well is a habit. Last season, we talked about the fundamentals of style, right? Understanding your body, and the basics of color, and proportion…all that good stuff. Those things are all about the skill of style. Style is a skill anyone can learn, and you don’t have to be born knowing how to dress your body or what colors look good on you…you can learn those things–hopefully, after last season you have more knowledge than you did before, and that’s great.

But. That’s not all there is. You can have all the knowledge in the world and still struggle to put an outfit together. You can be an expert in dressing your body, and still have a closet full of clothes and nothing to wear. You can know what’s current vs dated, and still go through life feeling frumpy and blah.

I’ve seen this happen so many times in my career, and what I’ve found is that most women think the answer to their struggles is to learn more and buy more. Take another class, get some more advice, learn some more rules, or hit the stores or websites and buy new things. What happens is they know more so they feel like style should be easier, but it still isn’t–and they have more, which in theory should make getting dressed easy, but it still doesn’t, and this reinforces the idea that they’re just not good at this, and maybe style truly isn’t for them. It can be really defeating. 

But here’s the thing. What most women miss on their quest for better style is the second part of my little quote–the habit of dressing well. They treat their style knowledge and skills like this separate, compartmentalized thing that they’ll pull down from the shelf and dust off when they really need it–and because they don’t NEED it all that often, it’s hard every time. Think about it this way. Let’s say you want to learn to ride a bike. You take a course, you buy the bike that the top bicycle influencer says you need, and you learn everything there is to know about the technique of riding your bike. But you only get on that bike and start pedaling the day of the bike race you signed up for, or on the day your friends say “let’s go for a nice long bike ride”. How successful would you feel? Probably not very. You’d say “I’m just not good at riding a bike–after all, I learned how, so it should be easy, it looks easy for everyone else”. See where I’m going with this?

On the other hand, let’s say you buy a cheap used bike on Facebook marketplace, you watch a 15-minute YouTube video on how to ride a bike, and then you just get on and go for it. And every day, you make a habit of going for a 10-minute ride. You’re not focused on the correct hand placement on the handle bars, or how many RPMs you’re pedaling, or how far you’re going…you’re just riding the dang bike, whether you have a reason to ride your bike or not. Which approach do you think is going to make you feel like a successful bike rider in 6 months? 

If you said the second one, you’re right. A consistent habit beats technical knowledge every single time. A consistent habit paired WITH technical knowledge is how you find success the fastest, in case you think I’m telling you knowledge doesn’t matter. I’m not. I’m saying it’s not a substitute for a habit.

Habits do a couple of things–first, they serve as practice. If you only practice the skill of dressing your body, or putting stylish outfits together when it matters–like right before a job interview, or a friend’s wedding–it will always feel hard, and probably not successful. Consistent habits give you daily practice–when the stakes are low. Then, when the stakes are higher, your skill is more developed, and you’re able to be more successful. Habits hone your skills.

The second thing habits do is that they reduce the energy you spend thinking about the skill. In the Style Circle, after our members take the Signature Style course, and define HOW they want to look, they spend a lot of energy looking at pieces they want to buy, deciding if they fit their personal style guideposts, or they spend energy putting outfits together that meet those guideposts. It’s something they’re actively thinking about. However, over time, it becomes second nature, and they spend NO time thinking about those things. It just happens. The skill of identifying things that are their style becomes second nature. Habits put your skills on autopilot.

In my experience though, this is something that holds a lot of women back. It can feel unnatural or even superficial to actively think about your clothes, or your outfits with that much energy. It goes back to “women should just be good at this, why do I have to work so hard”, and what we often don’t realize is that that period of awkwardness and forced practice doesn’t last forever. 

So many women don’t keep going to get to the other side of it, where style isn’t something they have to think about, it’s something that just happens because it’s become a habit. You just have to stick with it long enough to get through the awkward part–so you can get to the autopilot part.

So that’s what we’re talking about this semester. Creating a habit of style–or simply taking your knowledge, and putting it into practice in your everyday life so that it becomes second nature. We’re going to talk about some of the ways you’re making style harder than it needs to be–and how to fix it. I’ll share some practical ways to make your everyday style better, and we’ll talk about HOW to build that effortless, get ready for anything wardrobe you’ve always wanted. 

This season is all about taking action and making style easier in real life, creating a habit you don’t have to think so hard about. 

Over the next few months, you’re probably going to hear the phrase “dressing well is a habit” a few times, and if you’re thinking “I don’t need to dress well, I don’t go anywhere special”, I want you to stop right there. This is important, and without understanding this one thing, you’re going to miss a lot this semester, so I need you to hear this.  Dressing well does not mean dressing up. Let me repeat that–dressing well does not mean dressing up. You can dress well without ever putting on heels or uncomfortable pants. You can dress well in athleisure clothes–or heck, even pajamas. 

One of the biggest blocks for women is this idea that style, or dressing well means wearing blouses and blazers and pants with actual buttons and zippers. It doesn’t. Dressing well simply means feeling put together no matter what you’re doing or where you’re going–AND liking the way you look. That’s it. So, if you want to feel more stylish every single day, no matter what, that’s the first thought you need to embrace, otherwise, you’re going to spend big chunks of your life not feeling stylish, because you’re not dressing up. They’re simply not the same.

Now I want to switch gears a bit and talk about the most important ingredient in any habit, and because effortless everyday style is really just a whole bunch of habits strung together, it’s the foundation that everything builds on. You ready?

For any habit to stick, it has to be useful and rewarding–it has to do something for you. Let’s take brushing your teeth–I’m going to go out on a limb and assume this is a habit you do a couple of times a day, right? Good, glad we’re on the same page. WHY do you brush your teeth? Good breath, good oral hygiene–whatever. Point is, there’s a reason you do it, and you get something out of it that’s important to you.

Even bad habits give you something. Scrolling Instagram when you should be working, or cleaning your house? We can all agree it’s not productive, so why do we do it? Because it gives our brains a break, or a dopamine hit. We get something out of the habit. 

If you want a new habit to stick, one of the best things you can do is identify WHY you’re doing it, or what you want to get out of it. This is what keeps you going when it would be easier not to–when it feels awkward, or difficult.

To help get you ready for this semester of everyday action, I want to help you uncover WHY style matters to you. This might be something you’ve never considered, or you might have brushed off with a superficial “I just want to look put together”. That might be true, but WHY do you want to look put together? What does that, or what would that give you? The deeper the reason, the more impactful it will be–the more it will help you. 

Here’s the thing about your WHY–your why doesn’t have to be my why. It doesn’t have to be why society or your mother says style should matter. It doesn’t have to be anybody’s why except yours. All it has to be is your actual, personal reasons– reasons that are meaningful enough to spark and sustain action. 

Because if you don’t know why style matters to you, you won’t put effort into learning the skill or developing the habit. Or you will for a while, and then abandon your efforts the minute you hit a roadblock, or life gets busy. 

Your WHY is the difference between

“I should care about what I wear”

and

“I want to care about what I wear because it matters to me.”

It’s the anchor for your habit. 

The other thing about whys is that it’s incredibly helpful to have more than one. Sometimes your why just doesn’t apply–and different situations call for different motivations. So, I want to share 5 different kinds of why’s–and you can pick the ones that resonate with you. Here they are in no particular order.

Number one–The identity why. This one answers the question–who am I and how do I want to show up? This is about creating a style that feels authentic, and personal, and tells people who you really are. Maybe you want to be seen as someone who is capable. Or creative. Or put-together. Or fun. It's easier to project your inner self when you look the part–and when you look the part consistently. Think about a woman you know who always looks put together. We all know one, right? Don’t you naturally assume she’s got other parts of her life together?  Identity whys are powerful because they tie your style habits to your sense of self–and if you’re someone who struggles with feeling like an imposter when you try to have more style, or break out of your comfort zone, this is an important one to focus on. Who are you, and what do you want to express through your clothes?

The second why is the emotional why–this one is about how you want to feel, or how you don’t want to feel. Maybe you want to stop feeling like you’re the last priority for everyone–including yourself. Maybe you’re tired of feeling frumpy or invisible, or bad about your body. Maybe you don’t want to start the day feeling disappointed and defeated, and you’d rather start the day feeling calm and in control. Emotional whys are powerful because what you wear affects your emotions and how you feel about yourself. If you’ve struggled with body image or feeling bad about yourself, or feeling invisible as you get older, having an emotional why can help turn things around–because you get to choose how you want to feel and dress to support that. 

Next up is the practical why–this one is about the real-life reasons for having better style. Maybe you want to make your mornings easier, or stop wasting money on clothes you never wear. Maybe you want to stop emergency shopping every time you go somewhere–or worse, saying NO when people ask you to go somewhere. Most women, when they think about effortless style, are really talking about this one. The ability to open their closets, have what they need, throw on something great in under 2 minutes, and love the results. When style only matters to you when all conditions are perfect, effortless style will never ever happen–effortless style a result of a lot of habits and a lot of practice. The practical whys are important because they connect style to real life problems you want to solve like wasting time or money, so if you’re someone who says I don’t have time for style, or I don’t have money to buy a lot of clothes, this is an important one. Over time, habits help you use those resources better.

The fourth why is the legacy why. Legacy whys are about how your habits impact the people around you–especially your kids. Maybe you want your daughters to see a woman who values herself enough to dress well even if she hasn’t lost the baby weight. Maybe you want your sons to see that their mom is an actual person, not just an ATM or personal chef. Maybe you want to model self-respect, self-care or joy in the everyday. Legacy whys are about what we give to others by how we treat ourselves, and they’re important because they’re a reminder that how we show up sends a message that goes far beyond the clothes.

Unless this is the first time you’ve listened to the show, it will come as no surprise to you that this is my #1 why. Growing up, it was clearly communicated to me, through both words and actions, that looking good and having nice clothes were reserved for times that the scale said it was ok. I vowed, as a mom of daughters, that my girls would never ever see me earning the right to look good or wear nice things. I want them to see me buying clothes I love even in times where I’m not feeling the best about my body. I want them to remember that I looked nice on days I didn’t go anywhere, and that I had fun with clothes. I want them to see me valuing myself no matter what. If it never crosses their minds that they have to be worthy of buying great jeans, or they never treat clothes as a reward for having the right body, I will feel like a successful mom. But because I want that for them, I have to do it for me. I have to live that why.

The last one–number 5–is my other big why, and that’s the energy why–and this is all about how you function, and go through your day. One of my favorite memes says “I yell at my kids less when I like my outfit”. It’s funny, because it’s true. I think we all want to pretend that what we wear has no impact on how we go through life, but that simply isn’t the case. Most people function better when they feel put together. Studies show you make better decisions, you procrastinate less, and you’re more productive when you dress better. Getting dressed is a powerful tool, and these energy whys are important because they show that what you wear affects more than how you look. If you’re someone who wants to increase your personal energy and impact everyday, this one is for you.

I know I’m a different person when I like the way I look. My energy is different, and I don’t just mean physical energy. I mean things like whether I’m more outgoing or reserved, and even how I deal with inconveniences. 

For me, dressing well (not up, just well) is a really simple way to make the most of my day…and that’s what these why’s are all about. Finding the things that resonate with YOU and motivate YOU to build the everyday habit of style.

Before we get to the homework, let’s recap these whys real quick. 

#1 is the identity why–this is all about using style to align who you are inside with what people see so that you can feel authentic, and show the world who you are

#2 is the emotional why-this is all about how you use style to feel how you want to feel, and to avoid feeling how you don’t

#3 is the practical why, which is about solving the real-life challenges that not knowing how to have style causes. 

#4 is the legacy why–it’s the messages you’re sending through your style to those around you that they will carry for decades to come

#5 Is the energy why–which is all about the effect your style has on how you approach life.

Your homework, big surprise, is to start to define WHY style matters to you. It can be something we’ve talked about today, or something totally random. My best advice is to choose more than one why, but you don’t need all 5. Pick ones that are honest, and true, and big enough to actually motivate you. In the end, you should be able to complete the sentence–style matters to me because __________________.

Then, as you’re going through your week, getting dressed each day, ask yourself if you’re getting dressed in alignment with your reasons. And if you find yourself saying “no, because I’m not going anywhere special”, ask yourself if you’re confusing dressing well with dressing up. 

The truth is, most of our lives are lived in the everyday…so don’t save style for times it matters. Your everyday matters, so get dressed for it. 

That’s it for this episode of the Everyday Style School. Thank you for spending time with me today.

If you’re ready to make style easy once and for all, I invite you to join my free workshop, Style Made Simple, where you’ll discover why style feels hard–and how to make it easy. You can sign up at freestyleclass.com, or through the link in the shownotes.

I’ll see you next time–and until then, stay stylish!