Jennifer Mackey-Mary: Hello Gorgeous! 

It's week 7 of The Everyday Style School: Summer Shorts–our weekly summer series sharing a quick style thought or tip to help you save money, save time, and get the wardrobe you've always wanted.

I'm your host, Jennifer Mackey-Mary. I've been dressing women for 25 years, and I'm on a mission to help you love the way you look every day. 

One theme we've touched on a couple of times in this series is the idea of style being this thing you put on when it "matters" and take off when you want to be comfortable vs style as a way of being. If you remember, we talked about the difference between dressing well and dressing up, and giving yourself permission to like what you like. Both of those are really important if you want to move from having stylish outfits to being a stylish woman and Today's tip is another piece of that particular puzzle. It's all about where to start if you want that transformation–which I assume you do, since you're listening to this show. So here's today's style truth– Stylish women don't wear ratty underwear. You heard me. I said what I said, And I'll say it again. Stylish women don't wear ratty underwear. As a matter of fact, stylish women have nice underwear, loungewear, and pajamas.

Today, I want to talk about why the things people don't see are actually more important to your style than the things they do and share a couple of things you can do to approach style differently. But first, lets go back real quick to the idea that style is either something you put on and take off or something you have all the time.

There's a quote from legendary basketball coach, and personal development expert John Wooden that says "The true test of a man's character is what he does when no one is watching". With respect to Coach Wooden, I'd like to borrow that for this conversation and change it up a little– The true test of a woman's style is what she wears when no one is watching"

If you want to be a stylish woman, THIS is where we need to start in order to flip the script. And I swear I can hear, all the way in my office in suburban Twin Cities Minnesota USA, women out there saying "Ugh, but I don't want to wear those fancy pajamas" or "nope, I'm not wearing uncomfortable bras". If that described your reaction to the idea that stylish women are stylish even when no one's watching, with love, you need to go back to the first episode in this series. You've got a mindset block that's telling you style means dressing up in uncomfortable clothes. It's ok, a lot of women are stuck there, but until you change that, if your life doesn't require dressing up in uncomfortable clothes, you're telling yourself you can't have style, and no matter how much you say you want a fabulous wardrobe for the way you really live, you'll never get there.

But even as I say that, I know convincing women to prioritize clothes no one sees is a tough sell. Just getting my clients into better bras was a challenge, and that's literally step one to looking better in your clothes. Over the years I've heard "I'm the only one who sees it, so who cares", or "I don't want to spend that kind of money on things no one sees". If you're skeptical about the importance of nice underwear, loungewear, and pajamas, I want you to just suspend that for a little while and hear me out. Let me make my case, and then you can decide if I'm full of it or not. 

To me, there are so many reasons these unseen pieces are important, but I'm just going to share three today. 

First, what you wear when no one's watching says a lot about who you believe you are. It's easy to dress up for others, but what you wear in private reflects your true self-concept. 

And when your true self-concept is vastly different than what you want the world to see, you'll often feel like you're putting on a costume when you try to be more stylish. Style feels performative when at your core, you see yourself as the hot mess woman in a stained tee and leggings, lounging on the couch who's too embarrassed to answer the door. It's human nature to want to feel authentic, so to erase the disconnect between the different parts of you, what normally gives is the cute outfits. And then, even though you have nice clothes that are appropriate for your actual day, you pass over those things and choose clothes that are closer to the woman you really think you are. 

The trick is to have as little gap between all parts of your style self as possible. So that when you get home from wherever you go, and change from your outside self to your inside self, you still feel like the same person.

Like I just said, one way to erase that disconnect is to dial down your outside style and not wear the nice things, which is what a lot of women end up doing whether they realize it or not, but another way, and may I say a better way, is to dial up your inside style. When you look and feel a little better when no one's watching, it doesn't seem like a stretch to make an effort when people are. You're far more likely to wear stylish outfits outside of the house if you're not a total trainwreck inside the house, because all parts of you are aligned and you stop feeling like a style fraud. This is really how you go from being a woman who has stylish outfits sometimes to being a stylish woman. You have to see yourself as a stylish person all the time, not just when it matters, and you can't get there focusing only on the outside style you.

The second reason these unseen clothes are so important goes a lot deeper than clothes–and it's about worthiness. Because here's the truth: what you choose to wear when no one else will see you is one of the clearest indicators of how much you believe you matter. Not how much you matter to your family, or your friends, or the outside world—but how much you matter to yourself. The moments when you get dressed in the morning, or change into something comfy at night, are full of little messages that tell you whether you believe you're worth caring for just as you are… or whether you think you only deserve attention and effort when someone else is around to validate it.

And let's be honest—this is a spot where a lot of women let things slide. Not because they're lazy or uninterested in style, but because they're busy, or tired, or taking care of everyone else. So we default to what's easy and available: the old bra that should have been retired years ago, the pajamas with the stain on the front, the leggings you're secretly embarrassed by. It doesn't seem like a big deal in the moment—but over time, those little choices send a message. And often, that message is, "I'm last on the list." I don't deserve nice things.

When you value yourself, the pieces that no one sees become an act of self-care and self respect. When you choose underwear that fits well, pajamas that feel and look good, and loungewear that reflects your style, you're not doing it to impress anyone else. You're doing it because you believe you are worthy of nice things, and feeling good. And these things don't have to be fancy, or uncomfortable. It's not about that. Its about finding things that make you feel good, both physically and mentally, and remind you that you're worth showing up for, even if no one's going to see it. 

Finally, the third reason these pieces matter is that they affect your mood, and how you show up in life. You know that feeling you get when your bra and underwear match? You instantly feel a little more put-together, a little more in control, like you've got your life together. That small, intentional choice—made early in the day—sets the tone. It's a private confidence booster that no one else needs to see for you to feel the effect. But here's my question–why save that feeling for special occasions? Why not make it a daily habit? It's kind of like making your bed every morning. Not only is your bed made, and that's a good thing…but you also become a person who makes her bed, which is the bigger win.  Having your bra and underwear match is great, but being a woman who's bras and underwear always match? Well that's the kind of woman I want to be. 

A couple of years ago, someone posted in the community about this topic, and said something like "jen was right, nice loungewear is important" and then told the story of how her dog got out at 10:00 at night, and the whole neighborhood rushed out to help. Well, she was new to her neighborhood, and this was the first time meeting people. Her point was that if she had been wearing frumpy comfies, she would have been embarrassed, and not wanted to engage. But because she had upgraded her loungewear, she was truly ready for anything and made friends with her new neighbors.

There's actually science behind this called enclothed cognition, which is the idea that what we wear influences how we think, feel and behave. Now, notice I didn't say "what we wear when people see us influences how we think, feel and behave"–it's all of your clothing choices. When you wear things that make you feel good, and like you've got your life together, you raise your energy and become a person who has her life together. But when you wear things that make you feel dumpy and frumpy and like your life is an out of control dumpster fire, your energy will match that, too. 

What you wear has an impact on how you show up…whether people see it or not.
At this point, hopefully you're on board with the idea that what you wear behind closed doors matters too, or at least you're intrigued with the idea, and wondering if I might have a point. 

And if that's the case, I want to wrap up with a few practical things you can do right now.

The first one is go through your drawers and get rid of anything you're embarrassed by. I'm talking the bottom of the barrel stuff. Maybe you'd like to upgrade everything, and that's a great goal, but for most people its unrealistic. So just start with getting rid of the worst of the worst. You know, when we do our closet clean out challenges, we always start with drawers–for a couple of reasons. First, it's an area that's often neglected in closet edits, and is usually in desperate need of a good clean out. But more importantly, this is where self-respect and self-care starts in your wardrobe, and I always want to set that tone from the beginning. The rest is easy.

Once you've done that, I want you to commit to wearing your best stuff for a week. We just got rid of the worst of the worst, now flip the script and focus on the best of the best. By this, I don't mean wearing things that aren't appropriate or applicable for the day you're really having. This is again where we make the mistake of thinking that dressing well means dressing up or dressing uncomfortably. I'm not saying wear the valentines day stuff under your clothes to the grocery store–unless you want to, in which case, have at it. I'm just saying wear your nicest, best fitting everyday underwear instead of the ones that have seen better days. 

Finally, make a list of what you'd like to upgrade. Do you want pajamas that reflect your signature style? Do you want loungewear that you wouldn't be embarrassed to chase your dog in? Is it time for an underwear drawer refresh? Don't buy everything at once, just know what you need so you can be intentional about adding it to your wardrobe. 

If you do these three things, you'll start to change the way you think about the clothes no one sees, and start to take an inside out approach to style, which, in the end, is what turns you from a woman with stylish clothes, to a truly stylish woman. 

That's all for this episode of Summer Shorts. I hope it inspires you to take a fresh look at this unseen part of your wardrobe. As always Remember that your everyday matters, so get dressed for it.  Thanks for listening, and I'll see you next week.

Jennifer Mackey-Mary [outro]: And that's a wrap. Thank you for listening today. If you're loving the Everyday Style School podcast, I'd like to invite you to become a member of the Style Circle. It's our monthly all-access membership that gives you everything we create to make style easy, so you can save time and money, have easier mornings, and more confidence all day long. You get our seasonal capsule wardrobe guides, all of the masterclasses we offer, and our exclusive members-only podcast, The Everyday Style School Extra Credit. Plus, you're invited to the Facebook community, where you can get even more style support and inspiration. I would love to get to know you and support your style journey. It's just $19 a month, less than the cost of a clearance shirt you're never gonna wear. Come join me and make your everyday style easier.