I get it. Not everyone can afford to hire a personal stylist. That’s why the True Style Substack exists: to give you the tools to style yourself the way a professional (I) would, at your own pace, in your own space. Part of that is, of course, my 21 Question System, which is a condensed list of the actually-way-more-than-21 questions I ask clients to build their Style Profile. These questions are meant to help you reflect on how you dress, how you would like to dress, and how to put it all together before you even purchase a thing.
After looking inward to figure out the basic tenets of your personal style, it’s time to move on to the second major step in the True Style process: The closet evaluation. Do not hop into the closet evaluation without evaluating yourself, first! After all, how do you know whether or not the things you own actually serve your personal style if you don’t really have a good grasp on what your personal style is, yet? Don’t worry, you can come back to this article, later. I’ll wait…(don’t forget to check out the follow-up, too, where I explain how these questions all contribute to the bigger picture of your personal style).
Okay, so now you get it. You know what you like, you have an idea of what you need, and you’re ready to start fine-tuning your wardrobe. So, let’s talk goals.
Why It All Matters
I’ve said before: it’s not really enough to just toss out things you don’t wear without understanding why you don’t wear them. The point of the closet evaluation is not to just get rid of stuff, it’s to, you know, evaluate. During this process, you should be taking special care to:
Familiarize yourself with what you own.
Take inventory of the things you have. Do you have too many tops and not enough bottoms, or vice versa? Is there anything in your closet you straight up forgot you have? What do you seem to have a lot of? What colors and fabrics do you seem to gravitate towards? Make sure to also try things on: does that dress fit you the way you want it to? Are those pants too big? I know it’s easier said than done, but, make sure the clothes in your closet fit you (both your body and your style) right now. If they need to be tailored, if you need to lose or gain a couple inches to wear it, or even if you plan to upcycle/DIY it on some later date, it shouldn’t be hanging out with the clothing you wear now.
Look at your wardrobe with fresh eyes.
As you’re familiarizing yourself with the things you own, and trying them on, try putting things together that you haven’t before. Get into the details: can you change this item by belting it or tying it in some way? Try some new layering techniques, or new color combinations. Hell, you could even try wearing an old dress as a top or a top as a skirt. Don’t be afraid to really get experimental. You never know, you might realize you already have what you need to create the look you’re aspiring to.
Understand your shopping habits.
Sometimes, it’s hard to get a good grasp on what exactly leads to us owning the things we own, wear, and don’t wear. As you’re looking at each item, ask yourself why you bought it: did you get it because it was on sale, or because you thought you’d need it for work or an event or something or other only to never get any use out of it? Did you really love it at one point and now you don’t? Whether you wear an item rarely or not at all, or multiple times a week/month, figure out why: is it the fabric, the color, the way it makes your body look? For the pieces that don’t work: how would they need to change to be more useful? For the pieces that do: take note! You’re gonna need those notes to…
Make a plan.
So, now, hopefully, you have a good understanding of what you own and how to style it, what you like and dislike about your wardrobe, and what you should be looking for. Time to pull it all together and make a plan. I stress the importance of lists a lot, but, actually writing down the things you (think you) need and want, and revisiting said list often and before making any purchases can help immensely, particularly with staving off impulses and building more effectiveness and versatility into your wardrobe. I suggest organizing your list in order of more immediate use and then adding your pure wants at the bottom. For instance, I have about 10 outfits already ready to go for when I buy the elusive perfect white slouchy boots, so I’m currently prioritizing those (aka, searching the internet far and wide for the perfect pair). However, before I can get much use out of the distressed denim shorts that are also on my list, I still need a couple pieces to pair with them. Basically, if you can wear it multiple ways as soon as you get it, it’s top priority. If you need to complete more of your list before you can wear it, it can wait.
Don’t forget the things that need to be upgraded and replaced, as well. Maybe you already have a black blazer, but you’d prefer one that’s more oversized or cropped. Maybe you just want to upgrade all those fast fashion basics to something more high quality. No matter what it is: put it on the list!
So, now you know why you need to evaluate your wardrobe (and do so regularly, I might add). The question now is: how? Let’s start with the most common, and the one that I use with clients:
Do It All In One
This, for many, is the easiest way to evaluate the wardrobe. Simply go through your closet and put items in piles based on what you want to keep, what you want to get rid of, and what you’re on the fence about. We’ve all done it at least once, but without considering why each item is going into its respective pile, you’ll find yourself doing it all over again sooner than you may like.
Once everything is organized, go through it again, and take note of all the things I mentioned before: ask yourself why you’re keeping one thing and getting rid of another; identify why you’re on the fence about some things, and why you’re so staunchly on one side for others; and—and this is most important—examine how everything makes you feel. From there, you can make your list and your plan.
The Analytical Approach
This one is for the more mathematical-minded: make a spreadsheet! Go through your wardrobe and list everything you own, including shoes and accessories. Set a reasonable time limit—say, 6 months to a year—and make an actual note every time you wear an item, as well as what you wore it with. After the time is up, analyze how often you wore each piece, your most common outfits, and what you didn’t wear, to figure out what you gravitate toward, as well as the current limitations of your wardrobe and why some things went unworn. Maybe you’ll find your priority is buying more of what you already wear; maybe you’ll resolve to buy things to go with what you don’t wear as much so that you’ll wear them more; or, most likely, you’ll do a little bit of both.
The Visual
For those of you who need to see things to believe (and process) them, commit to taking a picture of your outfit every time you get dress for a set period of time. The objective here is to not just see what you’re actually wearing, but to understand how you tend to pair things together and what your overall vibe/look is. This method is best if you set yourself a goal to wear everything in your closet at the same time, and take note of how you go about that, as well as what you can’t seem to style and, of course, what you need to add to be able to style it, or whether it’s worth keeping at all.
Turn The Hangers
This is one I’ve seen recommended all over Style TikTok, and it’s very useful if you 1. hang all your clothing, and 2. hang all your clothing well. It’s fairly simple: turn all your hangers backwards so that the hooks are facing out (rather than in like with normal hanging). As you wear things, hang them back the right way. At the end of a set time period, whatever hasn’t been turned correctly is assumed to have not been worn and therefore has no place in your wardrobe. As I said, this is great if you hang all your clothing correctly to begin with. Me and my mismatched hanging styles, however, do not vibe with this method, but it’s worth the mention.
The Hideaway
You know what they say: out of sight, out of mind. But, this final method exists to test that theory. A bit of a disclaimer: I don’t recommend trying this if you have ADHD, or struggle with object permanence (like I do…yes, even at my big age), as it can produce false results. But, if you not only have a decent memory (must be nice) and a pretty extensive closet, this may be the method for you.
Basically, hide everything you don’t wear very often, or, if you want to make it even more advanced: hide everything but your most basic of basics. Put it all in a box under your bed, or in the very back of your closet, or in an entirely different room altogether if you can. But, make sure it’s not staring you right in the face. When you get the urge to wear something you’ve hidden, simply…go get it. At the end of a set time period, everything that you didn’t dig out of its hiding spot has sort of weeded itself out, and you can determine from there whether it’s worth integrating properly into your wardrobe by figuring out how to style it, or if it has no place at all with the things you actually, literally reach for.
While I am staunchly against the yearly overhaul, a yearly evaluation of the things you buy and wear (and how you wear them) is one of the most powerful tools for building a better wardrobe for all the reasons I described previously and probably way more. Don’t take it for granted!