← The Everyday Style School
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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 that would pull it all together. It's like you're a sartorial Goldilocks. Everything's 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. 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 macky. 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 are getting ready for jeans and sweaters again. That's right, just like school, we are taking the summer off. But there are plenty of episodes in the back catalog that you may have missed or you 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 our last episode together 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 that 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 to you, 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 all the bells and whistles and layers and accessories. After that, I shared four non style habits that actually improve your style. And if you ask me, there are some real nuggets of wisdom in there that if you really practice them, will make your style so much easier. That is 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 are not using AI for style right now. It's important to be aware of some of the pitfalls and some of the blind spots as AI gains traction in overall 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 one yet, go check it out. I'm going to be referring back to it a lot today. The link is in the show notes. Anyway, we talked about how it's different than just getting dressed every day. It's getting dressed for your everyday life and liking the results. We talked about how to make everyday style easier. We really by doing two key things. Number one, making it a habit and number two, filling your closet with the right things so that the only option is to pull stylish outfits out of it. And that is where we are picking up today. Because filling your closet with the right things sounds like the secret to fabulous, effortless style. And frankly, it is the secret to fabulous, effortless style. But what does that really mean? Does it mean filling your closet with nice things, with expensive things, colorful things, trendy things, or even just 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 to be honest with you, most people still aren't doing, and that is having the right things for the way you really live. So that is what we are talking about today. How to figure out what those things even are. And once you do that, you can interpret them any way you want. You want color, cool, you want trends, fine. You want to buy everything from Gap Factory, you can probably do that too. Well, at least most of it. Once you understand this idea, you can start to right size your wardrobe so that whether you are scrubbing your deck, running errands, leading a meeting at work, or having dinner in a fabulous restaurant, you've always got the right thing to wear. And you can stop feeling like someone who's either trying too hard or not trying enough. Today I'm going to take you through the process of understanding your wardrobe and understanding your needs so that you can align them. And after that, there's work for you to do. And if you do it, I promise your wardrobe will get so much better. And if you don't do the work well, then I hope you at least enjoyed the sound of my voice for the next half hour or so and that maybe you take away a little nugget of wisdom. So today I'm going to break down the six categories of clothing that exist and tell you some of the biggest mistakes I see women make with this and how that makes style in the real world more difficult. And then I'm going to walk you through how to figure out what your closet actually needs. Because while there are six categories of clothing, I'm not saying you need all six or that you need exactly the same amount in 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 will share how to figure that out. So let's talk about these six categories. This concept is something that I saw on the Internet years ago, and honestly I wish I could remember where I saw it to accurately give credit it. But I have tweaked the original a little bit to focus more on casual clothes because a couple reasons. First, the world dresses up a whole lot less than it used to. And also everyday casual clothes are much, much harder to get right from a style perspective than dressy, workwear, event clothing, black tie, all that good stuff. These six categories are based on level of formality and utility or how they are used. You can put your own style into each one. I can and do have category one clothes that are current, polished and fun. And I could have category six clothes that are current, polished and fun. These categories are another good example of definition rather than expression, which we talked about last episode. So I'm going to define the categories and you're going to define it however your stylish little heart desires. Another thing though, to keep in mind is that even though the level of formality applies to the whole category, it doesn't mean all the clothes in that category can be used interchangeably. And I'll give you an example of what I mean right now as we kick it off with Category one. Category one is what I like to call function. First, these are clothes that you either buy or wear or with function in mind, you wear them when you are doing a specific thing. These are things like gym clothes, pajamas, swimwear, painting clothes. If you want to go paint a wall, you go put on your painting clothes, right? If you want to go swimming, you go put on your swimsuit. That's pretty self explanatory. After the last episode when I talked about scrubbing my deck in stylish clothes, I got a couple people asking, well, don't you have just like grubby painting clothes? And yes, of course I do. In reality, I don't do that much painting or hard labor So I only have a couple of shirts and maybe one pair of pants that got ruined in the wash and I kept for that purpose. And those things probably break my style guideposts, especially polished, although they probably started out cute. But yes, yes, I do. Everyone does. But things like my sun shirts, which are definitely a category, one item on, are current, polished and fun. My swimsuits are current, polished and fun. Gym clothes, same thing. And what I would say here is that this category is where all of the ratty I only wear them to clean kind of clothes live. But not all of the clothes in this category have to be or even should be ratty. The point here isn't how nice the clothes are, it's what you're doing doing in them. And to me, these clothes aren't really part of your quote unquote wardrobe. Yes, they are clothes, and yes, 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 guess I'll wear my swimsuit instead. Which is an example of how clothes can be in the same category but not be interchangeable. But also, you don't say, huh, I think I'm going to wear my gym clothes to that graduation party. No, these clothes stay in the category for the most part. The only time I see crossover, at least in my own wardrobe, is some gym clothes that can be a part of my athleisure wardrobe for me in the cooler months, there's almost no crossover between what I would wear to like run errands or or wear to the gym. But in the summer I've got some athletic shorts that I do wear to the gym or to go hiking in. But if you would not wear it when you are not actively working out, it is category one. If you would happily wear that item when you are working out and when you're just out and about. It belongs to category two, which is very casual or errands casual. This category is usually comfort first. And these clothes are 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 want to look overly styled. These are clothes that you would wear to run to Costco or walk the dog, do light housework, obviously nothing bleach related or work from home or even wear to go on a road trip in. These could be things like Athleisure or sweatsets, basic hoodies, tees, sweatshirts, athleisure bottoms, sneakers. These are the clothes that you wouldn't be embarrassed to be seen in, but you probably wouldn't choose to wear to a social event. So going back to last episode when I talked about grabbing dinner with my husband after buying mulch, those were category two clothes. If I was going on a dinner date, no, I would not wear category two clothes there. Which brings us to category three, which is upgraded casual or everyday casual. The shift from category two is that the style is dialed up a little bit and the focus on comfort is dialed down a little bit. Category 3 clothes are everyday clothes that look like you made a little bit of an effort. It does. Doesn't mean these clothes are all of a sudden uncomfortable. It just means that's not the focus anymore. These clothes look a little bit more intentional. Could be things like jeans, graphic teaser sweatshirts, beyond basic knit tops, casual dresses, denim alternatives like chinos or casual linen pants, everyday handbags, simple jewelry, flats or fashion sneakers. In category two, it could be actual athletic sneakers or fashion sneakers, but this one is fashion sneakers. Category 3 clothes go places like casual lunches, coffee dates, shopping, everyday kind of social plans, book club, maybe a very casual office or casual church. And I think some of you are saying, but 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. You do you. This list is not meant to be prescriptive and tell you what you should be wearing to anything you, 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. Moving on to category four, which is smart casual. And again, we are 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 in styled, even if they're not super dressy. This is what you wear when the occasion feels just a little bit more special than every day or you want to look a little bit more refined. And this is where this category is where I would put most business casual offices. But it could also cover nicer dinners, date nights, a casual shower or party, and a lot of events and theater performances, especially when they're held like during the day. Category 5 is dressed up or professional. These are clothes that you would wear to dressier offices, interviews, work presentations, cocktail parties, weddings, fancy restaurants, and evening events. That kind of thing. Typical pieces in this category include, but are not limited to suits or dressy separates, structured dresses, cocktail attire, heels or special flats, clutch purses, more structured fabrics, a lot more sparkle and shine. And this category is usually where implied or expressed dress codes start. And then we come to category six, which is dress to the nines or formal. This is true formal wear, black tie for formal weddings, galas, that kind of thing. And I'm not going to list what's acceptable here because we did an episode on decoding the dress code that you can check out. We'll link it in the show notes. But honestly, of all six, this is the easiest one to understand and get dressed for. Because just like category one, it is specific and there is very little crossover between other categories and very little room for interpretation. And also, this is where there's a lot of help to help you dress for it and buy for it. These pieces are not a part of your versatile mix and match wardrobe. They just are what they are. You wear these things when you need them and you don't wear them when it's not those occasions. Okay, so there you have it. Six categories of clothing based on level of formality and their utility. Now let's talk about some of the biggest wardrobe mistakes I have personally seen women make over the years and how they apply to this specific framework. First, and I mentioned this before, I shared the six categories, but it's something I see women struggle with a lot. And, 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 one, 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 four, which is that smart casual category. 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. Things where you want to look put together and a little bit special but not super dressed up. And she was having a hard time because everything she bought looked like what she would wear to her business casual office. And she didn't want to feel like she was going to work when she was at a social event. Both of those 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 every day? Or how do I find clothes that. That make it feel like I'm not going to work every day? And I was like, well, by buying clothes that you wouldn't wear to work, it needs to have something different. More color, a little sparkle or shine, a fun pattern. I don't know, a little bit of a sheer sleeve or a more open neckline. Maybe a dress. If you don't always wear dresses, these things don't have to be more formal or necessarily dressier. They still need to 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 just don't look right. They just look off. With categories one and six, it is 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 are not wearing your favorite blazer to weed your flower beds or trying to make a graphic tee look black tie. Right. But when it comes to the other categories, there's definitely crossover, and there should be crossover. It's one of the ways that you get a more versatile mix and match wardrobe. But when you mix a two with a five, it doesn't always work. Even if the colors match, even if the pieces are all your style, even if they're all basics, sometimes the level of formality, especially in the fabrics, just looks off. One of my favorite clients of all time came to me years ago, probably over a decade at this point. And she is a successful, accomplished woman with a very good job who realized over a decade ago that she just wasn't looking the part, but she didn't know what was off. So we went through some of what she was wearing to work, and she showed me one of her go to outfits that she would wear to a department meeting, which, by the way, she was the head of. And it was black pants and a blazer. Nothing weird there, right? Wrong. Because they were black hiking pants. They were a poly nylon blend with the reinforced stitching and probably, like the little zippers on the pockets. And I was like, nope, absolutely not. Never, ever, ever again. Burn them. Those pants were between a 1 and a 2, and the blazer was a 4 or a 5, and together they added up to a 0. And sorry, my friend. You know I adore you, and you have come so far, and I hope we can laugh at those early outfits. But the point is, plain black pants aren't just plain black pants. This style, the fabric, the cut, they all change how the pants look and what they're appropriate for. And it's the same thing with things like layering tees. You really can't put the same thing under a category 5 blazer to wear with your suit that you put under a category two hoodie. A good guideline here is that pieces from categories next to each other play well together. Pieces from categories two 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 risk it. For example, I mix twos and fours regularly. I love a sweatshirt paired with relaxed trousers or a long dressy coat over a sweatset. But a blouse and sweatpants wouldn't work nearly as well. Even though that is the same thing. It's. It's a two and a four. It just doesn't work. So more than one category apart, you got to be really careful. More than two categories apart? Yeah, be careful, be careful, and probably don't do it. 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 and not right increases as well. So there is a risk reward calculation that you have to do. But the first step is just understanding where those pieces fall and understand that not all pants, all tees, all sweaters, all whatever are created equal. The 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 that you'd wear the pieces for. Right. Category two for me feels like Saturday mornings. Category four for me 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 a lot of 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 everywhere you go. And what I see is women thinking their personal style in categories 1 and 2. It doesn't matter at all. And then they have a different style for category three and the social part of category four, and then a different style for the workish parts of categories four and five, and then the social side of categories Five. And all of category six is just whatever works in the moment. Whatever dress they find at Nordstrom, whatever. And there are a couple of problems with this, but the biggest one is that in order to have that 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 twos and fours work together in large part because they're both speaking current, polished and fun. But if you have category threes that speak feminine, subtle, and romantic, and category fours that speak bold, trendy, and edgy, they're not going to mix so well. Right. Even though the categories are close to each other, when this happens, you need more clothes. You end up with a lot of unworn or underworn pieces, and your outfits can look really, really disconnected when you try to mix things up, reinforcing the idea that you're just not good at style, when in reality, that has nothing to do with it. It's just that the different categories of your wardrobe are so siloed that they can't talk to each other. The fourth mistake I see women make is lumping categories one and two together. Category one is all about function first, and it can include things that are a little ratty, Things you would wear to scrub the floors or give the dog a bath without worrying that you're going to wreck the things you love. Like I said, I've got some of those things. Everyone does. But often category one bleeds into category two, that very casual category, and the standards that you would have. If you realize that category two is an outside category A, people might see you category, those standards just disappear. And that is 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. We Just Associate Category 1 is comfortable stuff categories. Everything else is dressed up. But that's not true. You don't have to choose between looking good or being comfortable. What you do need to do is delineate between category one clothes and category two clothes. If you ask me which category most women I talk to are lacking in their wardrobes, it would be category two. And this is what I'm talking about when I talk about putting the right things in your closet. I have good category 2 clothes. It's probably the best part of my wardrobe. And that right there. That's the secret. All right, mistake number five, the last one is that women buy category four wardrobes for category Two to three lives. Category four clothes are so fun, aren't they? They're so pretty. They are what the best versions of ourselves would wear. They're what we would wear to brunch or that cool new restaurant in town. If only we went to brunch or that 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 that we would wear when it made 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 we shop without an understanding of what we're getting dressed for, we buy clothes for this category 4 woman. The clearance rack is a great source of category four clothes. That fun skirt, the cute blouse, and. And there is nothing wrong with any of those things as long as your closet category four is right sized for your life's category four. I used to love buying clothes for category four. Love it. But I would go into my closet and I would feel kind of bad. Like there was a woman in there with a really fun life. She just wasn't me. I needed really cute category two and category three. And there is another way we end up with Too much Category 4 and not enough twos and threes. 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 that idea again. Here it goes. That dressing well means dressing up. And this is an idea I think I might spend the rest of my career trying to dismantle. It's simply not true. And it is keeping you from dressing well for the way you really live. If you are not a person who ever wears a blazer instead of a denim jacket, you will not become one by simply 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 is not a category on this list that is inherently unstylish or inherently stylish or inherently more stylish than another. And if moving up in categories was all you needed to do to have more style, why wouldn't you just wear ball gowns or suits all the time? I mean, that would solve the problem. If that's the reasoning. By being more dressed up, you are more stylish. Then the Answer to being more stylish would just be be more dressed up. And when I say it like that, it sounds pretty silly, doesn't it? The trick is, I know I've said this before, probably in this episode, 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. Glad you asked. Let's talk about it. The first thing I want you to do is actually stop looking at your closet and at 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 money fixing the clothes. So here's what I want you to do. And yes, this is your homework. It's very easy, but it takes a while, which is fine because you've got the whole summer to do it for 30 days. And actually this is better if you do it like 60 or 90, but let's just go 30 for 30 days. I want you to give each day a number between 1 and 6 based on the categories I shared earlier. You can use your phone's notes app. You can use a piece of paper, your calendar, or whatever works for you. It doesn't have to be fancy. If your whole day was one number. For example, my entire day yesterday was a two. Just put that. If you have days that require you to change. For example, my work day today is a three, but I have a thing tonight that's a four jot both down. If you just want to wear something different, but it's the same category, you do not have to record that. Don't overthink this. If you felt like your day was a three, but you were wearing something that I said was a four, just call it a three. The point of the categories is not to list everything or exclude everything. And the goal isn't perfection or surgical precision. It's just to recognize patterns. And once you've got 30 or more 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 five and six, just lump those together. You can also do a cursory check of category one as well. But women who listen to this show are mostly category two, three, and four kinds of ladies. So I do want you to sort those separately. And this is not a closet edit. We're not looking at. Does this Fit. Can I wear it five ways. None of that. We're just trying to understand the relationship between your wardrobe and your lifestyle. And once your clothes are roughly sorted, match the closet to the data. If your days were mostly twos, but you don't have any twos, I think we found the problem. If your days were almost never fours, but your closet is full of fours, I also 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 first part is about quantity understanding if you have enough clothes for the way you really live or too many things for things you never do, and identifying those gaps and the mismatch and solving that right problem first, that quantity problem first. It'll help you shop smarter, spend better, and end up with a wardrobe that makes it easy to get dressed for anything and everything. And that is just a quick and easy way to do a simple, simple category audit. It's just a piece of paper, 10 seconds a day and a half an hour or so once you've got some data. But if you want to go a little bit deeper and if you want to start to identify the quality of your wardrobe within those categories, you can do that by simply putting like a little happy face by the number if you liked your outfit that day, or an X or a sad face by the number if you didn't like your outfit. For example, if you had a category three kind of day and you wore a great category three outfit, just put a little star or a happy face if you had a Category 4 kind of day and you struggled to get dressed or you hated what you wore, you felt frumpy all day. Give it a little X or a frowny face. And 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 with the way you really live, you can feel Focus on creating the style you want to see throughout your entire wardrobe. And that is how you get a ready for anything wardrobe and a style you love. All right, friends, that is it for this episode and this season of the Everyday Style School. Thank you for spending time with me today. 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, and maybe even having a little bit more fun with it. Speaking of which, Speaking of easier, better style, the Summer Capsule Guide is being released May 29th. This is your roadmap for effortless style in categories 2, 3, and 4. No painting clothes, no ball gowns. Just real style for real women living real lives. I will see you in September. Have a wonderful summer. I have got a great season planned for fall. I'm so excited about it. And until then, remember your everyday matters. So get dressed for it.