Jennifer Mackey-Mary: Have you ever felt like you never have the right thing to wear? No matter what, you’re always a little overdressed or a little underdressed, or your closet is missing that one key thing. It’s like you're a sartorial Goldilocks–everything is a little too this, or a little too that, and in the end, all you want is an outfit that feels just right. Turns out, building that “just right” wardrobe isn’t magic. It’s easier than you think, and it’s what we’re talking 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 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!
It is the LAST episode of the Spring Semester. I can’t believe that after this, we won’t be together until we’re getting ready for jeans and sweaters again! That’s right, just like school, we’re taking the summer off, but there are plenty of episodes in the back catalog that you may have missed or want to re-listen to, and besides, I’ve got a couple of things up my sleeve for summer that you won’t want to miss, but yeah, this is it before our break. And I think–or at least I hope–that you’re going to like this one.
This season has been all about making it easier to get dressed–and like the results– for your real life. We started with the idea that dressing well is a habit and we talked about the fact that every habit needs to have a reason for doing it–something you get out of it, because the truth is, if you don’t think dressing well matters, or you don’t know why it matters, you’re not going to do it. Then I gave you my BASIC formula for style that’s simple, but not boring–or, how to elevate your everyday without lots of bells and whistles and layers and accessories. After that, I shared 4 non-style habits that actually improve your style, and if you ask me, there are some nuggets of wisdom in there that if you really practice them, will make style so much easier. That’s a good one to re-listen to. After a quick detour to talk about some trends for the season, we spent a couple of episodes on AI and style–and even if you’re not using AI for style right now, it’s really important to be aware of some of the pitfalls and blindspots, as AI gains traction in all aspects of our lives. Finally, in our most recent episode, we covered the concept of everyday style. By the way, if you haven’t listened to that yet, go check it out-I’ll be referring back to it today a lot. The links are in the shownotes. Anyway, we talked about how it’s different than just getting dressed everyday–it’s getting dressed for your everyday life and liking the results–and we talked about how to make everyday style easier–really by doing two key things. 1) making it a habit and 2) filling your closet with the right stuff so that the only option is to pull stylish outfits out…
And that’s where we’re picking up today, because filling your closet with the right things sounds like the secret to effortless style, and frankly IS the secret to effortless style, but what does that really mean? Does it mean filling your closet with nice things, expensive things, colorful things, trendy things, or the right basics?
Honestly, no. I mean, it could—but there’s another step before that, and it’s one that I talk about ALL the time, but let’s be real–you’re probably still not doing–most people aren't, and that is having the right things for the way you really live. So that's what we’re talking about today–how to figure out what those things even are... .and once you do that, you can interpret them anyway you want. You want color? Cool. You want luxury bags? Fine. You want to buy everything from the Gap Factory? You can do that too–well, probably most of it.
And once you understand this, you can start to right size your wardrobe so that whether you are scrubbing your deck, running errands, leading an important meeting, or having dinner at a fabulous restaurant, you’ve always got the right thing to wear, and can stop feeling like someone who’s either trying too hard, or not trying hard enough.
Today I’m going to take you through the process of understanding your wardrobe, and understanding your needs, so you can align them. After that, there’s work for you to do, and if you do it, I promise your wardrobe will get so much easier and better. If you don’t do the work, I hope you at least enjoyed the sound of my voice for the next half hour or so.
Today, I’m going to break down the 6 categories of clothing that exist and tell you some of the biggest mistakes I see women make with this, and how it makes style in the real world more difficult. Then, I’m going to walk you through how to figure out what your closet actually needs–because while there are 6 categories of clothing, I’m not saying you need all six, I’m just telling you what they are. It’s up to you to decide if you need clothes in that category, and how MUCH you need in that category, and I’ll share how to figure that out.
Let’s talk about the six categories. This concept is something I saw on the internet years ago, and I wish I could remember where to accurately give credit, but I’ve tweaked the original a little to focus more on casual clothes, because the world dresses up a whole lot less than it used to, and frankly, everyday casual clothes are harder to get right from a style perspective.
These categories are based on level of formality and utility–or how they’re used. You can put your own style into each one. I can, and do, have Category 1 clothes that are current, polished, and fun. And I could have level 6 clothes that are current, polished, and fun. These categories are another good example of definition, rather than expression, which we talked about last episode. I define the category, you express it however your little stylish heart desires. Along with that, even though the level of formality applies to the whole category, it doesn’t mean all the clothes in it can be used interchangeably–I’ll give you an example of what I mean right now, as we kick it off, with–
Category 1 is what I like to call Function First. These are clothes you buy, or wear with function in mind. You wear them when you’re doing a specific thing. These are things like painting clothes, swimwear, gym clothes, pajamas…. If you want to paint a wall, you go put on painting clothes. You want to go swimming, you pick a swimsuit. Pretty self-explanatory.
After the last episode, where I talked about scrubbing my deck in stylish clothes, I got a couple of people asking, “Well, don’t you have just like grubby painting clothes?” And yes, I do. In reality, I don’t do that much painting, so I only have a couple of shirts and one pair of pants that got ruined in the wash that I kept for this purpose. Those things probably break my style guideposts–especially polished–although they started out cute. So yes, I do. But my sun shirts, which are definitely a category 1 item, ARE current, polished, and fun. My swimsuits are current, polished, and fun. What I would say here is that this category is where all of your ratty, I only wear them to clean, clothes live, but not all of the clothes in this category have to be, or even should be, ratty.
To me, these clothes aren’t really part of your “wardrobe”. Yes, they’re clothes, and you need them, but clothes in this category serve a defined purpose that nothing else in your wardrobe really does, and you don’t wear them outside of that defined purpose. It’s not like you say “oh, my painting clothes are in the wash, so I’ll wear a swimsuit instead”--which is an example of how clothes can be in the same category, but not interchangeable. But also, you don’t say “I think I’ll wear my gym clothes to that graduation party”. No, these stay in this category for the most part. The ONLY time I see crossover is some gym clothes that can be a part of your athleisure wardrobe. For me, in the cooler months, there’s almost no crossover, but in the summer, I’ve got some athletic shorts that I do wear to the gym, or to go hiking, but if you would not wear it when you’re NOT actively working out, it’s a category one. If you would happily wear it both ways, it belongs to category two.
Which is, Very Casual, or Errands Casual– This category is usually comfort first, and they’re what you reach for when you want to look presentable, and put together, but you want it to be easy, and you don’t necessarily want to be or look overly styled. These are the clothes you’d wear to run to costco, walk the dog, do light housework–nothing bleach-related, work from home, or go on a road trip in. These could be things like athleisure or sweat sets, basic hoodies, tees, sweatshirts, athleisure bottoms, sneakers. These are clothes that you wouldn’t be embarrassed to be seen in, but you probably wouldn’t choose them for a social event. Going back to last episode, talking about grabbing dinner after buying mulch? Yes to category 2 clothes. Going on a dinner date? No.
Now we come to category 3, which is upgraded casual–or everyday casual. The shift from category 2 is that style is dialed up a little, the focus on comfort is dialed down a little Category 3 clothes are everyday clothes that look like you made an effort. It doesn’t mean these clothes are uncomfortable, it just means that’s not the focus. These clothes look a little more intentional. This is jeans, graphic tees or sweatshirts, beyond basic knit tops, casual dresses, denim alternatives like chinos or joggers, casual linen pants, everyday handbags, simple jewelry, flats, fashion sneakers–category 2 could be actual athletic or fashion sneakers, this one is fashion sneakers,
Category 3 clothes go places like casual lunches, coffee dates, shopping, everyday social plans, book club, maybe a very casual office or casual church.
Now some of you are saying–this is what I wear to run errands and go to my kids’ games, and to that I say fantastic–that is totally your right. This list isn’t meant to be prescriptive and tell you what you should be wearing to anything. You wear what feels right to you. This is just meant to show you that there are levels of casual wear, and you can use that knowledge to make sure your wardrobe has the right things in it.
Category 4 is Smart Casual–we’re dialing up the formality here with things like blazers and jackets, nicer dresses, polished denim, heels or loafers, blouses or refined knits, relaxed trousers. This category is about polished pieces that create elevated outfits that feel intentionally put-together, even if they’re not super dressy. This is what you wear when the occasion feels a little more special than just everyday, or you want to look a little more refined.
This is where I’d put most business casual offices, but it also covers nicer dinners, date nights, a casual shower or party, a lot of events and theater performances..
Category 5 Is Dressed Up/Professional–these are clothes you’d wear to dressier offices, interviews, work presentations, cocktail parties, weddings, fancy restaurants, evening events.
Typical pieces in category 5 include, but are not limited too, suits or dressy separates, structured dresses, cocktail attire, heels or dress shoes, more structured fabrics. This category is usually where implied or expressed dress codes start.
Category 6 is Dressed to the Nines–or formal.
This is black tie, true formalwear–for formal weddings, galas–that kind of thing. I’m not going to list what’s acceptable attire here, because we did an episode on decoding the dress code, that you can check out, we’ll link it in the shownotes. Of all 6 this one is by far the easiest to understand, and get dressed for–just like category 1, it’s specific, there’s very little crossover between other categories, and very little room for interpretation. These pieces are not part of a versatile mix-and-match wardrobe. They just are what they are.
There you have it–6 categories of clothing based on level of formality and their utility. Now let’s talk about some of the biggest wardrobe mistakes I’ve personally seen women make over the years, and how they apply to this framework.
First, and I mentioned this before I shared the 6 categories, but it’s something I see women struggle with a lot–and that is thinking all the clothes in one category are interchangeable. It sounded pretty obvious when I said you wouldn’t wear a swimsuit to paint your bedroom, right? Even though those pieces are both category 1, they’re not the same. They DON’T serve the same purpose. It’s the same thing in other categories too, and the biggest one I see women struggle with is category 4–Smart Casual. Recently, I had a style circle member ask a question in style coaching that perfectly illustrates this. She was struggling to find some things for spring events–like baby showers, graduation parties–that kind of thing…where you want to look put together, and a little special, but not super dressed up. She was having a hard time because everything she bought looked like what she’d wear to her business casual office, and she didn’t want to feel like she was at the office when she was at a social event.
Both of these things are category 4 kinds of activities in terms of level of formality, but the clothes are not the same. They weren’t serving the same purpose, or giving the same result. And her question was “how do I not feel like I’m going to work everyday”, and I was like, by buying clothes you wouldn’t wear to work. It needs to have something different–more color, a little sparkle or shine, a fun pattern, a little bit of a sheer sleeve, a more open neckline. It didn’t have to be more formal, or dressier–it needed to still look polished, just in a less workwear way.
The second mistake I see women make is jumping across too many categories, and the results are outfits that simply don’t look right. With categories 1 & 6, it’s pretty easy–yes, there’s a little crossover between athletic and athleisure pieces, and a little crossover between black tie and black tie optional, but you’re not wearing your favorite blazer to weed your flowerbeds, or trying to make a sweater look black tie. But when it comes to the other categories, there’s definitely crossover, and there SHOULD be crossover–its one of the ways you get a more versatile, mix and match wardrobe. But when you mix a 2 with a 5, it doesn’t always work–even if the colors work, even if the pieces are all your style, sometimes the level of formality, especially in the fabrics, just looks off. One of my favorite clients came to me years ago, and this is a successful, accomplished woman with a very good job who realized she wasn’t looking the part, but didn’t know what was off.
When we went through some of what she was wearing to work, she showed me one of her go-to outfits–that she would wear to a department meeting–which she was the head of. It was black pants and a blazer. Nothing strange there, right? Wrong. They were black HIKING pants. A poly/nylon blend, with the reinforced stitching, and zippers on the pockets. I was like, no. Absolutely not. Never again. Those pants were between a 1 and a 2, and the blazer was a 4 or a 5. Together, they added up to a zero. Sorry, friend, you know I adore you, and you’ve come a long way, baby, and I hope we can laugh at those early outfits.
Point being–plain black pants aren’t just plain black pants–the style, the fabric, the cut–they all change how the pants look and what they’re appropriate for. Its the same with things like layering tees. You can’t put the same thing under a category 5 blazer that you put under a category 2 hoodie.
A good guideline is pieces from categories next to each play well together, pieces from categories 2 levels apart need to be approached with intention and a very critical eye, but beyond that, to be on the safe side, I wouldn’t.
For example, I mix 2’s and 4’s regularly–I love a sweatshirt paired with relaxed trousers, or a long dressier coat over a sweat set. But a blouse and sweatpants wouldn’t work quite as well–even though that’s a 2 and a 4 as well.
The further away the pieces of your outfit are on the category scale, the more stylish the outfit could be, but also the chance that it’s just going to look off increases as well. There’s a risk/reward calculation you have to do–but first, you have to understand where your pieces fall, and understand that not all pants, all tees, all sweaters, all whatever are created equal.
Next big mistake is having different personal styles for each category. One of the things that defines a category is the part of your life you’d wear the pieces for, right? Category 2 feels like Saturday mornings to me. Category 4 feels like Saturday nights.
One of the first classes our members take is Signature Style, which helps create a roadmap for a cohesive, mix-and-match wardrobe that helps you have more style with less stuff. But
a big struggle our members have, that they almost have to deprogram in their minds is that you can be who you are in all parts of life–that yes, you express it differently in different situations, but you can still have your authentic style in all parts of life. What I see is women thinking their personal style in categories 1 and 2 doesn’t matter at all, they have a different style for category 3, and the social part of category 4, then a different style for the workish side of category 4 and category 5, and then the social side of categories 5 and 6 is whatever works in the moment.
There are a couple of problems with this, but the biggest one is that, in order to have a cohesive, mix-and-match wardrobe that allows you to use more of what you have, the pieces need to talk to each other, and they can’t talk to each other if they’re not speaking the same style language. My 2’s and 4’s work together in large part because they’re both speaking current, polished, and fun. But if you have category 3s that speak feminine, subtle, and romantic, and category 4s that speak bold, trendy, and edgy, they may not work so well, even though their categories are close to each other. When this happens, you need more clothes, you end up with a lot of underworn pieces, and your outfits can look really disconnected when you try to mix things up, reinforcing the idea that you’re just not good at style, when really, that has nothing to do with it.
The fourth mistake I see women make is lumping categories 1 and 2 together. Category one is all about function first, and it CAN include things that are a little ratty–things that you can wear to scrub the floors and give the dog a bath without worrying you’re going to wreck things you love. Like I said, I have some of those things, everyone does.
But often, category 1 bleeds into category 2—the very casual category, and the standards you would have if you realized that category 2 is an outside category, a people-might-see-you category, just disappear. That's when you have to hide at the grocery store. This is why women feel like they have to choose between looking good or being comfortable. You don’t. But you do need to delineate between category one clothes and category 2 clothes. If you asked me what category most women I talk to are lacking in their wardrobes, it would be category two. This is what I’m talking about when I talk about putting the right things in your closet. I have good category two clothes, there’s the secret.
Ok, Mistake #5 last one is that women buy category 4 wardrobes for category 2-3 lives. Category 4 clothes are so fun, aren’t they? They’re what the best versions of ourselves would wear. They’re what we’d wear to brunch, and the cool new restaurant in town–if we only went to brunch or the cool new restaurant in town. Category 4 is where aspirational buying comes in for a lot of everyday women. This is what we tell ourselves we’ll wear when it matters. We WANT to be the woman who throws on a blazer instead of a denim jacket, or a blouse instead of a sweater–so when we shop, especially when we shop without a plan, or an understanding of what we’re getting dressed for, we buy clothes for her. The clearance rack is a great source of category 4 clothes. The fun skirt, the cute blouse. And there’s nothing wrong with any of those things–as long as your closet’s category 4 is right sized for your life’s category 4.
There’s another way we end up with too much category 4, and not enough 2 and 3s. When women want to improve their style, they think it requires moving up in categories, rather than just wearing better things in the categories that match their lives. This is the idea that dressing WELL means Dressing uUp, which is an idea I think I might spend my entire career trying to dismantle. It’s simply not true.
If you are not a person who ever wears a blazer instead of a denim jacket, you will not become one simply by putting a blazer in your closet. If you reach for athleisure pants every single day when you work from home, stop buying trousers, hoping that will change things. Just buy a more modern denim jacket. Replace your worn-out leggings with nice athleisure pants. There isn’t a category on this list that is inherently unstylish or inherently stylish. And if moving up in categories was all you needed to do to have more style, why aren’t you wearing a suit or a ball gown right now? That would be silly, wouldn’t it.
The trick is to have stylish clothes for the way you really live, not clothes for a version of life that isn’t based in reality.
So how do you do that? Great question, let’s talk about that.
The first thing I want you to do is actually stop looking at your closet and your wardrobe, and start looking at your life–because a lot of women think they have a clothing problem, when what they really have is a mismatch problem between their clothes and their lives, and until you understand the life, don’t spend your time or your money fixing the clothes.
Here’s what I want you to do–and yep, this is your homework. Its easy, but it takes a while, which is fine–because you’ve got the whole summer to do it! For 30 days, I want you to give each day a number between 1 and 6 based on the categories I talked about earlier. You can use your phone's notes app, or a piece of paper, whatever works for you. If your whole day was one number, for example, my entire day yesterday was a 2, just put that. If you have days that require you to change–for example, my workday today is a 2, but I have my daughter’s senior awards dinner tonight, which is a 4–jot both down. If you just want to wear something different, but it’s the same category, you don’t have to record that.
Don’t overthink this. If your day felt like a three, but you were wearing something I said was a 4, call it a 3. Again, the point of the categories isn’t to list or exclude everything, and the goal isn’t perfection or surgical precision…its just to recognize patterns.
Once you’ve got 30 days of data, head to your closet and roughly sort your wardrobe into categories. If you don’t have a lot of need for categories 5 and 6, lump those together. You can do a cursory check of category 1 as well, but women who listen to this show are mostly category 2, 3 and 4 kinds of ladies, so I want you to sort those separately.
This is not a closet edit– we’re not looking at, does this fit, can I wear it 5 ways–none of that. We’re just trying to understand the relationship between your wardrobe and your lifestyle.
Once your clothes are roughly sorted, match the closet to the data. If your days were mostly 2’s but you don’t have any 2’s, I think we found the problem. If your days were almost never 4’s but your closet is full of 4’s, I think we found the problem.
A few weeks ago in an email, I shared a style tip, talking about the difference between a quantity issue in your closet, and a quality issue. This is about quantity–understanding do you have enough clothes for the way you really live, or too many for things you never do, and identifying the gaps.
Solving the right problem first will help you shop smarter, spend better, and end up with a wardrobe that makes it easy to get dressed for anything and everything.
This is the quick and easy way to do a simple category audit. Just a piece of paper, 10 seconds a day, and a half hour or so when you’ve got some data.
Now, if you want to go a little deeper, and start to identify the quality of your wardrobe in those categories, you can do that by simply putting a little happy face by the number if you liked your outfit that day, or an x by the number if you didn’t like your outfit. For example, if you had a category 3 kind of day, and wore a great category 3 outfit, give it star, or a happy face. If you had a category 4 kind of day, and you struggled to get dressed, or hated what you wore, give it an x. Then, when you sort your clothes by category, just ask yourself– do these clothes light me up? Do I love them? Do I feel good in them? I don’t need a full closet edit to tell you which clothes I feel great in, and I guarantee you don’t either, but this will help you identify which categories of your wardrobe need a quantity boost AND a quality boost.
Once your closet is aligned for the way you really live, you can focus on creating the style you want to see through your wardrobe, and that’s how you get a ready for anything wardrobe.
That’s it for this episode AND THIS SEASON of the Everyday Style School. Thank you for spending time with me–I hope after the last few months, you’re thinking about your everyday style in a new way–finding simple ways to make it easier and better. Speaking of which, the Summer Capsule Guide is being released May 29–it is your roadmap for effortless style in categories 2-4. No painting clothes, no ballgowns. Just real style for real women living real lives.
I’ll see you in September–I’ve got a great season planned for fall–and until then remember, your everyday matters, so get dressed for it!