Jennifer Mackey-Mary: If you don’t have fit, you don’t have style. I wish I could take credit for that quote, because it’s so true, but I believe credit belongs to Stacy and Clinton from the US version of what not to wear. Regardless of who said it though, fit is fundamental to style. You can follow all the trends, buy all the right things for your body shape, and all your best colors, but if your clothes don’t fit you, your style isn’t coming together. So today, I’m going to share 5 big mistakes I see women make when it comes to fit. Let's get started!

Hello gorgeous, welcome back 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, budgets, and lives, I know great style isn't about following one-size-fits-all advice - it's about learning what works for you.

If you listened to my last episode, you know that this semester, we’re focusing on style fundamentals–the basics that make style simple in the long run. Truly understanding these things is like the difference between being able to follow a recipe, and actually knowing how to cook. Yes, you can go through life just following recipes, lots of people do. But when something goes wrong, you won’t know why, and you’ll never be able to make a meal without a recipe. On the other hand, when you learn how to cook, you know how to fix a recipe gone wrong, or avoid mishaps altogether. You know how to get the flavors you want, and most importantly, you don’t need your phone to cook dinner. Style is the same way. You can follow the wear this not that lists, or get a box of clothes sent to you every month…or you can learn how to do it yourself, and not be dependent on those things forever. Mastering the fundamentals is the way to go, so that’s what we’re focused on. 

Also in that episode, I gave you a preview of some of the topics we’ll be talking about this season, and I told you we’d be talking about fit, because it truly is the most fundamental of all the fundamentals, so that seems like a good place to start. 

This season we’re talking about things I’ve probably talked about before, so it’s my goal to try and bring you something new. That might prove difficult to do, but I’m going to do my best. I’ve dedicated an entire episode to the basics of proper fit, which is a very old episode, but everything in it is still true, so we’ll link that in the shownotes, you can go check it out. Which means that today, I want to bring you something else, so I thought I’d talk about where fit goes wrong…the most common issues I’ve seen over the years that are keeping women from having better style, even when they’re buying clothes that should be great. 

I’ve got 5 of them, and before we get started, I just want to remind you that we are wrapping up our semester with a Q&A episode, so if you have style questions you’d like me to answer, send it in! 

Alright…the first mistake women make when it comes to fit is confusing fit with fit.

And if you’re like, well, now I’m confused, let me explain. When it comes to clothing, the word “fit” has a lot of different meanings. First, it can be slang for outfit–like “fit check”. It can also mean “to be of the right size” (thank you dictionary.com), which is what we’re talking about in this episode. But it can also be another way to describe the cut of the cut of the garment, which is where the confusion comes in.

In this last use of fit, or cut, what we’re really talking about is how close to the body the item is SUPPOSED to sit. So you have things like a body con fit–which is supposed to be super close to the body, then you have fitted, which should be close to the body, then regular fit, relaxed fit, and oversized fit. That’s not all of the cuts, or the fits out there, but that gives you an idea of the spectrum of fits, or cuts that are out there. In jeans, I’m sure you’ve seen things like relaxed fit and baggy fit, right? That’s what we’re talking about.

What happens is that to get a more relaxed cut–something roomier and less close to the body, oftentimes what women will do is just size up. I see this all the time on instagram–influencers saying “size up for a more relaxed fit”, and to some extent this can work. Especially if you’re in between two sizes. You can choose the bigger one for a more relaxed fit, the smaller for a more tailored fit. I ended up buying the same tshirt in two sizes this summer. I couldn’t figure out if I liked the the way the medium or the large looked more. I wore the medium when I had bottoms with more volume to balance things out, and the large when my bottoms were more fitted. But in both sizes the hallmarks of proper fit were still there–again, go check out that old episode.

However, this isn’t always a winning strategy because as a garment increases in size, so does everything else. Sleeves get longer, armholes get lower, neck openings get bigger…all these things that throw off how a garment FITS–meaning “to be of the right size”. 

To get clothes that have the closeness to your body that you’re for, you have to adjust with CUT, not size. So if you want jeans that don’t hug your hips and rear, instead of buying regular fit jeans in a size or two too big, buy relaxed or loose fit jeans. This is how you get the fit you want without sacrificing the hallmarks of proper fit. When a top is an oversized cut, it still fits somewhere. The neck is the right size, the sleeves are the right size, it’s the right length. Just sizing up throws the whole thing off and makes you look sloppy.

And if you’re thinking, but I see that on instagram and pinterest all the time, I’m just going to be brutally honest with you and tell you a) there’s a ton of manipulation that goes into a lot of those photos and b) this is a strategy that doesn’t work as well for real women in their 30’s and beyond as it does on social media. 

So how do you fix this one? The best thing you can do is read labels. Start reading item descriptions online as if they were food labels–like what is this thing made of? I was shopping for Fall Capsule pieces, and I came across a sweater that just said “Soft Tunic Sweater”--ok, that doesn’t give us much info, does it? But in the description it says this cozy sweater combines comfort and style with its relaxed fit”. There you go. That’s the word we’re looking for. Then, use those words to get the cut you want, instead of trying to get there by manipulating the size. 

Mistake #2 goes along with that, not understanding the relationship between size and proportion. Back in the day of low and mid-rise jeans, I used to struggle a lot, because I have a long torso, so a lot of tops left me with an inch or two of belly exposed, which is really not what I was going for. I remember being in a store and finding a top I loved, but I just needed more length, so even though I know better, i was like, I’ll try it in a bigger size, in order to get more length. One size up helped, but didn’t solve the problem. Two sizes up solved the problem, but now the shirt didn’t look right any more. 

In my summer shorts series that we just finished, I noticed a theme that came up a few times was solving the right problem, and this is an example of that. The problem wasn’t that the top didn’t fit me, it was that it was too short for MY body. The shirts proportions didn’t match mine, and by sizing up, I was solving the wrong problem.

Let me give you another example, one I’ve personally seen play out hundreds of times with my clients. Women with curvy bodies sized up in pants to get them to fit their hips, and then ended up with a huge gap in the back. Why? Because they were solving the wrong problem. It wasn’t that the pants were too small, it was that they didn’t fit their proportions right. When we put them in jeans and pants with the correct proportions–ie, curvy fit pants, they almost always went down at least one size–the pants fit in the hips, no more gap in the back. 

This applies to petites, too. I’m not joking when I say that almost all the one on one clients I’ve worked with in the last couple of years who have come to me because they just feel frumpy and nothing looks right have one thing in common. You know what it is? They’re petites who aren’t buying petites. 

And more than once, when I tell them this is the entire problem, I’ve heard, but I have things tailored..and by this, they mean they have their pants hemmed. But petite clothing is an entire set of proportions that cannot be fixed by buying a size smaller, or by tailoring one part. The pocket and knee placement is different on jeans, and that doesn’t change when you hem your pants…you can shorten a sleeve but are you fixing the armhole too? If not, it’s still not going to fit you properly. 

You’ve got to understand your body’s proportions, and find clothes that mirror them. If not, your clothes will never fit right. 

Fit mistake number 3 is thinking sizes mean anything at all. The other day I was getting dressed, and I had a little chuckle to myself when I realized the pants I had on were a small, the tank I was wearing was an extra large, and the cardigan over it was a medium…and they all fit perfectly. I wouldn’t have wanted to size up or down in anything. 

The truth is, sizes are completely meaningless beyond being a starting point, but they lead to ill fitting clothes in a few ways.

The first being unwilling to size up because you think a letter or number says something about you as a person. I remember talking to a potential client a few years ago–we ended up not working together, and you’ll see why in a second. She reached out to me because she had gained weight, nothing fit, she was feeling bad about herself, and was struggling to get dressed everyday. Ok, cool, we can work with that. Except…she also refused to buy anything bigger than a 16, and she would not consider plus sizes. Okayyyyyy. She said that was just her mental threshold, she couldn’t do it, wouldn’t do it, that was it. She was not plus size, and refused to buy plus sizes. So as long as I could find clothes that fit her and made her feel good at the current size she was wearing, she was in. At that point, I was out.  

This is an extreme example of making sizes mean something, but I saw it dozens of times when shopping with clients, and suggesting we try a bigger size. So many times they would just reject what could have been a great item, because they refused to size up. 

The flip side of that is women refusing to believe a smaller size fits them. Like, I can’t be a small, I’ll get the medium. Often this is rooted in some strong feelings about vanity sizing, which I’m going to come back to in a minute, so hold that thought. This is especially prevalent when online shopping–even if the fit says relaxed or oversized, even if all the reviews say it runs big, we still think no, that won’t be true for me, I’ll just get my regular size–and then we keep things that actually don’t fit. And when it doesn’t fit, you look bigger than you are, which reinforces the idea that you’re a larger size, and the cycle continues. Stop shopping with your mind mirror–she’s a lying liar who lies.

Before we get to vanity sizing, let’s talk about the third way that ascribing meaning to sizes hurts your style..and that is, assuming you’re the same size everywhere, or even within one brand. Fun fact–the small pants and extra large tank I had on were from the same brand. I have extra smalls and extra larges from Zara and everything in between and you know what? I don’t care. Now, it does mean I won’t shop online, because zara is like a box of chocolates, you never know what you’re going to get. I accept their lack of consistency and work around it. Would it be lovely if sizes were consistent between stores and brands, or even within stores and brands? Yes, but that’s not the way it works, and you can either spend your time being mad about it and wearing ill fitting clothes, or accept it and work with it. Again, reading online descriptions and reviews tells you so much, but you have to accept that sizes are fluid at best, and sometimes even meaningless.

So let’s talk about vanity sizing. If you’re not familiar, vanity sizing is this idea that retailers increase the size of the clothes, while keeping the label the same to make us feel good about ourselves. Do I believe in vanity sizing? Yes and no. I completely agree that clothing sizes have gotten bigger over the years. I know we’ve all heard “Marilyn Monroe was a size 16” and its supposed to be a message of body positivity and size inclusivity, and I’m all for those things, but let’s be honest, Marilyn Monroe was not a twenty first century size 16. Sizes have changed. I worked with a client who had a lot of Talbots clothes from decades past that were a size 10-12, and when we to Talbots to refresh her wardrobe, she was a size 6. So yeah, things change. 

But is that because Talbots, or any other brand wanted her to feel better about herself, or is it a reflection of the changing customer? Women are bigger now they were in the 50’s, or even a couple of decades ago, and I have this idea that sizing is a reflection of the stores customer rather than a standard, unchanging measurement. Let’s say a medium is the middle, average size of the store’s customer. I understand its not, but go with it. Talbots average sized woman in 1995 looks different than Talbots average sized woman today. So did they change the size to make her feel better about herself, or did they change sizes to say this is the range of the typical woman who shops here. And maybe it doesn’t matter which came first, or what the reason is when you’re talking about sizes within one brand, but it does matter when you’re going from store to store

We have this idea that a medium should be a medium everywhere. That it’s somehow a standard measurement, but it’s not.Like I said, it’s a reflection of the brand, or stores, customer. A medium at Chicos is going to be very different from a medium at Aritzia. The average woman shopping at aritzia is in her 20’s. The average woman shopping at chicos is in her 50s and 60’s. She’s been through menopause, her midsection is a little fuller. Those women are different, but a medium in each store reflects that middle size of each customer base. 

So when people say “fits true to size” the BEST it can really mean is that it fits true to size for that brand or store, and the best you can really do is know what you usually wear in different brands or different stores and use that as a starting point. 

The solution to all of this is to spend less time and energy wondering why sizes aren’t consistent, and worrying about the letter or number on the tag, and instead focus on knowing your usual size within your favorite brands, and use that as a starting point to find things that fit properly. And I know you’re thinking “but it’s so hard to do that online”. Yes, yes it is. And it isn’t going to change. Your choices are to shop in person, be committed to buying a couple of sizes and returning the ones that aren’t right, or accept ill fitting clothes. That’s pretty much it. 

Moving on to the 4th fit mistake women make-and that is, not understanding how fabrics affect fit. This happens in a bunch of ways. I know that if I’m choosing a top in a woven fabric, it’s probably going to be a size bigger than I would choose if it was in a knit–because the woven top doesn’t have the give to accommodate my broader shoulders, whereas the knit will move with me, making the smaller size a better option. 

But on the other hand, stretch isn’t always your friend–especially when there’s too much stretch. There’s a fabric I hate–and this is me personally, there’s nothing wrong with this fabric, but it’s a stretchy sweater. I hate a stretchy sweater. Case in point, the old navy so soft cardigan. Again, there is nothing wrong with this sweater, its actually a great piece, which is why I convince myself to try it every season, before remembering that it is not for me. This sweater has 3% spandex in it, which makes it clingy. I think my fellow apple sisters can agree that clingy tops are the worst, right? Every time I try one on, it clings, and I think, oh, it’s too small, so I try a bigger size, and you know what? It still kinda clings. That’s just what the fabric does. But a lot of women would just size up until the sweater isn’t clinging to the midsection..but at that point, the sweater just doesn’t fit you babe. Because it was never the size, it was the fabric. Try a sweater with rayon or modal instead–something to help it drape instead of cling…

I’ve seen this a lot with women whose lower bodies are bigger than their upper bodies when they try to wear blouses that end at the hip. Blouses are made from woven fabrics, which typically have no give, so the top is tight at the hips and women think they need to size up. Nope, it’s just the wrong fabric for your proportions causing a poor fit. Sizing up doesn’t help, because yes, maybe it fits a the hip, but it no longer fits at the neck and shoulders. 

Even the way fabric is dyed can affect the way it fits. Have you ever noticed black and really dark blue denim runs smaller than light or medium washes? Yep, you’re not crazy, they really do feel different, even if they’re cut the same. The dying process can make the fibers stiffer, less stretchy and more dense. So if you love a pair if black jeans and think, huh, I’ll just buy the same pair in blue, don’t be surprised if they end up stretching out to be too big. On the flip side, if you love your medium wash jeans, don’t be shocked if the dark blue version doesn’t fit the same way, and you need to size up.

The last mistake women make when it comes to fit is unwillingness to tailor. One thing I’ve heard a lot over the years is along the lines of “these pants weren’t expensive, I’m not going to bother tailoring them”, and on the surface, that makes sense–like it kind of feels wrong to spend almost as much altering your pants as you spent buying them in the first place, but another perspective is that, the less you pay for your clothes, the more likely things are to need alterations. The more mass produced something is, the less likely it is to fit YOU perfectly, and I think a good question to ask yourself is why did you buy it in the first place–for example, did you buy that skirt because it was cheap and who cares if it’s great? Or did you buy it because you loved it and want it to look as good as possible. In the first scenario, great–don’t bother tailoring it. In the second one though, it really doesn’t matter what you paid for it. If you love it and want to get as much wear out of it as possible, and you want to look as good as possible, tailoring is an investment. If you struggle with seeing the value in alterations, try looking at it like tailoring is an investment in you and your style, rather than an investment in the skirt. Not wanting to tailor something because it’s not an investment piece is being price focused, whereas being committed to having clothes that fit well regardless of how much you paid for them is being value focused, and if you don’t know what the difference between the two, I’ve got a bunch of episodes talking about this topic, but the short answer is, price is about cost, and value is about worth–how good does it look, how much wear can you get out of it, how good do you feel in it. 

One of our Style Circle members recently posted that she hasn’t bought or kept anything that doesn’t fit well in over a year, and she’s been shocked at the difference in the quality of her wardrobe. Everything looks better, and is more wearable, and she has more complete outfits just by focusing on the fit…and if you can get there right off the rack, great. I believe most women can improve fit by at least 50% without tailoring, just by doing the first four things we talked about today. But if your body is hard to fit, or you’ve done the best you can, but the fit still isn’t there, don’t discount how much value tailoring your clothes will add to your wardrobe. Yes, it’s an additional cost, but in a lot of cases, it’s absolutely worth it. 

Before we wrap up, I want to share a bonus mistake women make when it comes to fit and its one I’ve talked about before, but honestly, without fixing this one, the others are kind of pointless–and that is Knowing what fit actually looks like.

I remember working with a client who said on the pre-service questionnaire that she was a size 14, but when we worked together, she was closer to an 8 or a 10, so I asked her…what made you think you were a 14, or that these clothes fit you, and she said “well, they stay on my body”. Which, I mean, yeah, they did–sort of. Her pants were held up with belts, her skirts were sitting at her hips instead of her waist..but that’s a pretty low bar for fit. This is something that it’s difficult to see until you see it, but once you see it, you can’t unsee it. The episode I referenced earlier will help you start to know what to look for, but a really good thing to do is next time you’re in a store that sells clothes, try something on in the size you think you are, and then one size bigger, and one size smaller. Take pics to compare. Look for the gapping, pulling, pooling, draping that I talk about in that episode and start to recognize it. Once it clicks, you’ll see it forever.

Let’s recap what we talked about today.

First, if you don’t have fit, you don’t have style. You can buy all the right things, but if they don’t fit you well, it’s not going to come together the way it does in your mind.

The mistakes we make with fit often have to do with solving the wrong problem–whether it’s cut, proportion, fabric–we think a different size will make things better, and while it might solve one problem, that strategy causes other ones. Make sure you’re solving the right problem.

Don’t get attached to sizes. They’re a starting point, but beyond that, they’re meaningless. Get to know the sizing of your favorite brands, but even then, read the descriptions and reviews to get the right fit.

And if you can’t get a good fit off the rack, don’t be afraid of investing in your style by tailoring. Shift your perspective, and ask yourself if something isn’t worth tailoring, doesn’t really deserve a spot in your wardrobe–that alone might keep you from adding a whole lot of pieces that are fine, but don’t get worn.

Your homework for this episode is to look at the fit of your clothes. If you don’t know how they should fit, go listen to that oldie but goodie episode. Try different sizes on in a store, and every day you get dressed, objectively look at the fit of your clothes and see how you’re doing. Awareness really is the first step to mastering this style fundamental.

That’s it for this episode of the Everyday Style School. Thanks for spending time with me today. If you’re ready to make style easier and more fun, come join me in the Style Circle. It’s where you’ll get all of our classes, capsule guides and style tools, plus the support to actually use them. Become a member today at youreverydaystyle.com. I’ll see you next time–and until then, stay stylish!