Jennifer Mackey-Mary: Hello Gorgeous! 

The Everyday Style School is officially on summer vacation, but that doesn’t mean I’m going to leave you hanging for the next few months!  I’m taking a break from our longer episodes, but instead, each week you’re going to get a bite size episode sharing something I think will help you save time and money, and get the wardrobe you’ve always wanted.

If you’re new here, 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 thing I’ve noticed I say a lot on my show is along the lines of “something I say a lot is______” .Over the years, I’ve amassed a huge mental  database of tips and quips that I repeat over and over. But unless you listen to every word I’ve ever said on every podcast, every video, every Style coaching session you’ve probably missed some. And even if you’ve listened to every word I’ve ever said, there’s value in hearing things again so they can really sink in start to change your thoughts and habits around style.

This summer, I’ve rounded up what I think are 10 of  my best Style Tips or thoughts and I thought I’d share them with you in a series I’m calling The Everyday Style School: Summer Shorts. 

We’re going to start the series with something I think is so fundamentally important to understand, and that can have a huge impact on not only the way you look, but also how you feel about yourself. This one is really the foundation of everything we do at everyday style, so let’s get to today’s thought which is “Dressing well doesn’t mean dressing up”.

I know this concept seems pretty straightforward, and it is, but it’s something I saw women really struggle with on a deeper level when we did the Style Made Simple Challenge, so I thought it would be worth spending a little more time on. Today, I want to talk about how the two are different, what happens when we don’t understand the difference, and wrap up with what you can do to start embracing the idea that you can have the style you want even when you’re not going anywhere special.

Let’s start with the difference. Dressing up is what most of us think of when we hear the word "style." It's putting on your best outfit for date night, or wearing a suit for a work presentation Dressing up is temporary. It’s often tied to situations, events, or other people, and it’s something we usually save for when style “Matters”.  

There's nothing wrong with dressing up! I love a good dress-up moment. But if that's your only relationship with style, then you're basically saying that looking good is only for special occasions. That you can only have style when all conditions are right. 

Dressing well is completely different. It's about how YOU show up every single day, regardless of where you're going or what you're doing. It's about having clothes that are not only functional for the day you’re having, but make you feel good mentally as well as physically. It’s about YOU. Its personal.

When you're dressing well, you're not putting on an outfit you can’t wait to take off as soon you get home — you're just, living your life,  being the best version of yourself. Dressing well isn’t wearing a suit to the grocery store, it’s choosing flattering jeans over frumpy ones. It’s not different clothes that aren’t appropriate for your real life, it’s better versions of what you’re actually wearing. 

There are a couple of problems with conflating dressing up and dressing well. The first one is this, and I don’t know about you, but my life has gotten a whole less “special” over the years. Fancy date nights and Friday nights out as a single woman have given way to family dinners and early mornings at kids’s sports. Working from home means I no longer have to dress up, or honestly get dressed at all. Only a small fraction of my life requires dressing up. If I only dressed well at those times, I’d spend 97% of my life in clothes I didn’t feel fabulous in. That sounds awful.

But let’s dig a little deeper, because while I just said my life has gotten less special over the years, that isn’t really true. I have a wonderful life made up of special moments disguised as everyday life. Silly things like impromptu lunch dates with my husband of over 20 years to fancy places like Chick Fil A . When I like the way I look, my energy level is raised. I show up differently to my everyday life, and I am more aware and appreciative of the mundane moments that are actually much more meaningful. And that’s important, because 97% of the stuff that happens to me is in that “no need to dress up” category. 

Now if you’re thinking, thats all well and good for you, but I only feel the need to dress well when I see people, or when it matters, let me ask you this. Do you struggle to get dressed for those moments too? I bet you do, and here’s why. When your version of style is occasion specific, you probably find yourself shopping every time you have to go somewhere, buying things last minute, never having the right things or feeling completely finished. Because style isn’t a habit you’re developing in that 90+% of life, it’s almost impossible to pull off in those few and far between moments. If you don’t have fabulous jeans in your everyday life, you can’t throw on jeans and a cute top and feel good. Throw that cute top on with your frumpy everyday jeans, and you’re just going to feel frumpier. 

What happens to women who think style is something to bust out for special occasions is that they don’t feel good when it “doesn’t matter”, but they also don’t feel good when it does. 

Dressing well is about approach is to feel good when it doesn’t matter, and feel good when it does. Which would you prefer?

Here’s what I saw during the Style Made Simple Challenge. On Day 1, we talked about dressing well for the life you really live, and how it’s not for other people, it's about how it makes you show up differently, and everyone was on board! Yes! I want to feel good! Yes, Style matters to me for me! It was a very up with women moment and I loved it. But then during the week, during the daily outfit challenges I saw a lot of “I’m not going anywhere today, so I skipped this one” or “Im working from home, so I didn’t dress up” even though NONE of the challenges had anything to do with dressing up., and a couple of women even posted in the community about not caring what they wore when they weren’t doing anything special, so they were struggling with doing the challenge at all. And I’m not here to judge that, or be like I can’t believe they weren’t changed forever by a 30 minute video. No, just the opposite. It made me realize that this a mindset shift that takes some time and a habit that takes some effort. But it has to start with the idea that you can dress well for literally every part of your life without dressing up. 

So here’s what I want you to do: This week, I want you to think about how you can uplevel your daily outfits WITHOUT pushing yourself into a higher level of dressiness. For example, this morning as I was getting dressed, and I knew I’d be recording this episode, I decided to practice what I preached. I was wearing denim shorts and a cute graphic tee, which is kind of a default summer uniform for me, but I decided to switch out the shorts for red wide leg linen pants. It’s basically the same level of formality.  All the things I could have or would have done in my denim shorts I can do in my red pants, and actually, the pull on linen pants are MORE comfortable than jean shorts, but it looks a little more upleveled.

I want you to resist the urge to dress up on your quest to dress well.  It’s a natural tendency for our minds to immediately go there, and I can’t tell you how many clients I had to talk out of buying dressier clothes when we shopped together. I knew they just wanted to feel more put together, but I also knew if a mom who normally wore tees and leggings bought nothing but dress pants and blouses, she’d have nothing to wear on the Tuesdays she wasn’t going anywhere. My goal was to help her dress better for the way she really lived. 

So if you’re wearing jeans this week, choose the best jeans you’ve got. If you’re wearing a t-shirt, choose the one that fits the best and has the most style. Push yourself within the boundaries of what’s realistic and appropriate for your day. That’s how you dress well without dressing up.

That’s all for today’s Summer Shorts. I hope this mini episode inspires you to think differently about how you get dressed, and what you wear even when you don’t think it matters.  Remember, the majority of life is lived in the everyday, which is why I say 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.