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:
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