The last time I cleaned out my closet (which I have to do frequently, because I am an EPIC yo-yo dieter and every 6 months everything stops fitting), I was embarrassed by how much of the stuff I donated to Salvation Army without ever having actually worn it outside a dressing room.
I'm a very confused shopper. I don't know what size I am, due to a touch of body dysmorphia, and I shop with my gaping emotional void instead of my head. Often, I buy things because I want to be the kind of person who wears it, not because I actually am that kind of person.
In high school, when I was forever scouring the local thrift shops for velvet babydoll dresses and T-shirts with "Ed" written on the pocket, it was easy to talk myself into buying things that weren't quite right for me because, "HEY! It only costs a quarter!" This resulted in one weird-ass, over-stuffed wardrobe of dresses that sort of fit, if I wore a cardigan over them and button-up shirts that only buttoned up halfway, but no biggie, I'd just throw a T-shirt underneath.
But, yo, I'm 30 now, and while I believe in making epic mistakes in every decade of life, I'm kind of over buying stuff I never wear and am ready to move on to something exciting like unprotected sex. (Just kidding, I did that plenty in my 20s.) So as much as I do like to think about someone stumbling across a brand-new silk blouse from Zara with the tags still on and giving it a loving home, I've developed a few shopping rules designed to minimize unworn purchases.
Don't buy it if:
1. You can't wear it without Spanx.
I can't tell you how many times a sales person has told me, "Well you can always wear Spanx!" when I stood contemplating my belly fat in a particular garment while staring in the mirror. I started to write "well-meaning" sales person but they're probably actually just "meaning" to sell me something that doesn't look good on me, so.
I personally can't wear Spanx without balling them up and shoving them in my clutch midway through dinner, but I'm not anti-Spanx for anyone else. Do whatever you want with your body, get it surgically altered to look more like Barbie, I don't care. If you want to wear Spanx to streamline fit or feel more confident in a garment, then great. I just don't think it's a good idea to buy something that you would only feel comfortable wearing if half your internal organs are compressed.
If I have to wear Spanx in order to feel attractive in an outfit, then it's not really fitting my body in a way that makes me feel good. Instead, I look for styles and materials that flatter my body the way it is.
2. It's a jacket or a blazer and it doesn't button.
I know a lot of jackets and blazers look cute worn open, but I'm of the school of thought that if I'm not actually able close it, it doesn't really fit. CONTROVERSIAL? Ninety percent of the time blazers refuse to close over my giant boobs and it hurts to put them back, but I do it anyway. You don't have to button it, but you should be able to button it.
(Speaking of my giant boobs, I just got measured at Victoria's Secret and they told me I'm a 38DDD. Is that even a real thing? Internet bra nerds, go!)
3. It needs tailoring and you know you're the kind of person who never actually gets tailoring done.
So many fit problems can be solved with tailoring, but in order to fix something with tailoring, you have to take it to a tailor. After years of buying things that don't fit well with the rationalization that I can get them tailored, I have finally had to face facts that I am never, ever going to take an item of clothing to the tailor. Maybe in my 40s.
4. You can't sit down in it.
I am lazy, so I spend a lot more time sitting in my clothes than I do standing in them, yet I rarely bothered to sit down when I tried things on. Now, if it stretches too tight across my chest or stomach while sitting, or the skirt rides up to an obscene level, I put it back.
5. You don't know what you'll wear it with.
I have a beautiful pair of Bass saddle shoes that I bought from a little boutique in Brooklyn after the clerk oohed and aahed over how "me" they were. They live a sad, lonely life in a dark corner in the back of my closet because I knew when I bought them that I had no idea what to wear them with. Like with my pleather skirt or my metallic blazer, I just thought I'd eventually figure out something they go with, but guess what, I never did. Because as much as I like them, they don't really fit my style.
If you're really in love with a piece, go home and look at your closet and come back when you figure out how you plan to wear it.
6. It doesn't look good from the back.
Back fat is why I can't have nice things. On the one hand, back fat is nice because it's behind me so it's not like I have to look at it, but since the day I first stumbled into a dressing room with two mirrors, I do try to avoid fabrics that lovingly cradle my back fat like a very low and unsexy pair of back breasts. A butt check is also a crucial part of the shopping process, especially for those of us whose waist measurements lead clothing manufacturers to expect a hearty butt where there is none.
7. You already have three of them.
We all get stuck in a black skirt K-hole from time to time -- or gray sweaters or white T-shirts or whatever your personal fashion Kryptonite may be. You love it, you know it looks good on you, so you just keep buying it over and over and over again, ever searching for the platonic ideal of your beloved item. Having more than one version of a staple is wise, but a certain point you just don't need any more of them.
8. It gaps over the boobs even just a little.
You need room for your titties, girl. You just do.
9. You can't decide if you want it or not.
If you're waffling over whether or not to buy something, you don't love it. And if you don't love it, you're probably not going to wear it with any frequency. I take this concept to the next level by asking myself, "Do I want to wear this tomorrow?" If I'm not so excited about it that I want to put it on as soon as possible, I don't spend my money on it.
Talking about fit can be a touchy subject, so let me be clear. IT IS NOT YOUR BODY'S FAULT IF CLOTHES DON'T FIT YOU. It is the stupid clothes' fault! It is also the fault of the stupid stores that don't carry clothing that will fit a wide range of bodies.
As a size 14, I'm usually trying on the largest size in the store so if it doesn't fit, I can't go get another size to try. Sometimes nothing I like in an entire store fits me. The incentive is high to make it work.
So I understand that if you are a plus-size woman and you lack the resources to seek out (often expensive, sometimes hard-to-find) plus-size clothing that fits your body correctly, you may have to make it work with safety pins and cardigans and the like. That is also not your fault.
Do you disagree with my rules? It's OK, you can make your own. The goal is just to stop buying stuff that isn't perfect for you. Do you have stuff in your closet that you bought but never wear? Leave your shopping rules in the comment so I can get even better at this. (I literally just got a dress in the mail from ASOS that was a little tight and thought to myself, "Well I just joined a gym, so it'll probably fit in a few weeks..." so I obviously still need work.)