Never Return Anything Again: How to Buy Clothes You’ll Love to Wear

updated May 3, 2019
We independently select these products—if you buy from one of our links, we may earn a commission. All prices were accurate at the time of publishing.
Post Image
(Image credit: Heather Keeling)

Confession: I have a lot of anxiety about shopping for new clothes. I love adding new pieces to my wardrobe, but historically, I haven’t always been good at judging when I actually should or shouldn’t buy something. I’m totally guilty of buying basics like jeans or blouses that I later learn don’t actually fit comfortably for all-day wear, or on the other side of the spectrum, buying bold pieces that totally fit my personality, but don’t really work in my day-to-day life. The result? Tons of buyers’ remorse, wasted money and wasted time waiting in the returns line.

Fast forward to last summer, when I moved into a new apartment and completely cleaned out my wardrobe—doing so helped me become a lot more mindful about how I shop and how I see myself in the clothes I wear and try on. When I shop, I try to follow these tactics—I buy less, but I feel much more confident in my wardrobe.

Ask Yourself Key Questions

Before you buy anything, there are a few important questions you need to ask yourself from the fitting room—even if it takes you a little longer to try things on, you’ll feel a lot better about your buys:

  • What can I pair this with? If you’ve ever bought something you totally love only to realize you have nothing to actually wear it with (and no idea what to buy to pair it with) then you know this is an essential question to ask yourself. If you can’t think of at least two things in your existing wardrobe (or at least two things you would also want to purchase that would also get some regular wear) that you can wear an item with, it’ll probably be doomed to hang in your closet forever, so maybe it’s not worth buying. But if you can plan a few outfits with it and you really like it, go for it!
  • Where (and how often) can I wear this? Just as important as having other items to pair your new purchase with—you need to know that you’ll actually wear what you buy. Is it something you can wear in your usual day-to-day, or something that you might wear to a special occasion someday even though you have no actual concrete plans? If you can get some at least semi-regular wear out of it, you’re good to go. If you can’t imagine yourself wearing it except in a dream scenario, put it back. (Alternately, if you absolutely love it but can’t actually see yourself wearing it—and it’s reasonably priced for your budget—take this as an opportunity to push yourself out of your comfort zone and wear it anyway. You’ll thank yourself later!).
  • Is this easy enough to clean for my lifestyle? Have you ever bought something that you love and want to wear all the time, but then realize after a few wears that it’s impossible to clean? Same—and there’s nothing like finding out your favorite sweater is hand-wash only, knowing full well you don’t have the time to commit to actually doing it. Check the care instructions on the tag before you bring it to the register, and think realistically about your lifestyle and whether or not this new purchase fits in with your routine.
  • How does wearing this make me feel? Above all else, how you feel in your clothes is the most important thing to consider. If you put something on and it makes you feel even a little bit weird or self-conscious about yourself, take it off and put it back on the rack—if you doubt how confident you are in it, you’ll never wear it, and when you do wear it (say, on laundry day, or when you’re feeling optimistic enough to give it another shot) you won’t feel your best. You’re supposed to wear your clothes, not let them wear you. Only buy the things that make you feel like a boss, because that’s how you deserve to feel all the time.

Try Different Perspectives

Looking at yourself straight on in a fitting room mirror? Definitely not enough to get a true feel for your clothes (ask anyone who’s ever loved something in the fitting room only to bring it home, go to wear it and realize they actually hate it). To avoid post-purchase regret, try these tactics before you leave the dressing room:

  • Move Around (and Do the Sit Test) Move around, pose in different ways, and look at yourself from as many angles as possible to really get a feel for what you’re trying on—both in looks and in comfort. And most importantly, if there’s a bench inside your fitting room, take a seat in the clothes you’re trying on (if there’s no stool or bench, try squatting). You’ll be able to tell if things bunch or ride up uncomfortably, so there will be no surprises later on when you’re actually wearing them in real life.
  • Take Selfies… Yes, Seriously! One of the best ways to get another perspective of what you’re trying on is to take selfies. You don’t have to post them or share them with anyone else (although feel free to text your best friend for a second opinion—sometimes it helps!) but just taking them and looking at them can help you see yourself in a different light—maybe when you looked at it in the mirror you were unsure, but seeing the clothes you’re trying on in a photo makes you totally fall in love with it. Snapping a few pics only takes a minute, and it can definitely help.

When in Doubt, Use Accessories

If you’re drawn to bold, unique pieces of clothing but don’t quite feel confident wearing the things you love, try channeling your desired aesthetic in your accessories, not in your actual clothes. Buy clothing that you feel truly comfortable and confident in, and then spice things up with interesting pins, jewelry, bags or shoes. It’s a way to wear the things you love without overwhelming or limiting yourself to one specific look, since accessories add so much extra versatility to your wardrobe (and it can also help you ease yourself into wearing the bold clothing you admire!).