Exactly What to Wear When You’re Trying on a Ton of Clothes

Allow me to set the scene: You’re in a stuffy, brightly-lit dressing room struggling to remove knee-high boots, unbutton your button-fly skinny jeans, and pull them off over your ankles–all while wearing an itchy wool turtleneck sweater and aluminum-free deodorant. You’re sweating and your heart is racing because it feels like you’re taking forever just to take your own clothes off, let alone actually trying some on. A question echoes from the depths of your perspiring forehead: Isn’t shopping supposed to be fun?

It rarely feels that way when you’re not dressed in a strategic fashion beforehand. I realize it sounds counterintuitive to spend time thinking about what to wear for the purposes of finding other stuff to wear, and yet I can confidently say that doing so can be the difference between accomplishing what you set out to do and departing with nothing but a sweaty neck and a sense of defeat.

After years of trial and error, I have finally perfected the ultimate shopping-day outfit strategy–an approach that facilitates an optimal dressing room experience. Keep scrolling for six tips.

1. Carefully Consider Your Undergarments

Skin-colored high-waist cotton underwear is the best underwear for trying on clothes, hands down. Avoid anything with spandex because it clings and will slip as you’re taking other garments on and off (if you’re trying on a slip dress or anything silk–FORGET IT). Don’t stress about underwear lines–full coverage is best in this case because you’re trying something on that dozens of other people have also probably tried on. I also like to wear a tank top–also cotton–over a skin-colored bra (silhouette can vary based on what kind of bra you typically wear). The tank is important because occasionally you’re shopping with friends and want to open the dressing room door without feeling naked standing there. They’re also useful if you’re just trying on pants.

2. Do. Not. Wear. Skinny. Jeans

Skinny jeans are the epitome of hard-to-get-on-and-off, which means they are an automatic obstacle to easy retail shopping. We all know that the moment you leave the dressing room after trying on tons of stuff is the moment you spot the perfect item you didn’t see before. Suddenly you’re weighing the temptation to go back in and try it on versus the challenge of peeling off your skinny jeans once again. This dilemma could have been avoided in the first place if you’d worn a pair of pants more conducive to the occasion. I would suggest something with an elastic waist–potentially these track pants, these joggers or these trousers.

3. Keep the Top Simple and Avoid Static-Prone Knits

I will never forget trying on a slew of dresses before a high school dance and crying because by the last one my hair was standing straight above my head like one of those mini troll dolls. My mistake was entering the dressing room clad in a static-y knit, but now I know better. I recommend avoiding cashmere and/or wooly knits of any kind. Chunky knits or knits with a tight turtleneck are generally a bad idea, too, because they’re an arm workout and if you wear makeup you’ll get it all over them. Instead, layer a half-zip or cardigan (easy to pull or button on and off) over the aforementioned tank top (or long-sleeve T-shirt if it’s cold).

4. Stay Clear of Extraneous Embellishments

I’ve lost beloved earrings in dressing rooms, so this comes from the heart. Wear studs if anything–never dangly ones (they get caught on the clothes) or hoops (ouch). If you’re going to wear necklaces, avoid anything with crystals or prongs. I suggest a simple chain or strand of beads. Lastly, try not to wear rings, especially if they’re not properly fitted. I lost my mother’s band once because it slipped off my finger in a dressing room…. (I guess I lose stuff a lot, huh.) Learn from my mistakes!

5. Slip Into Some Slip-Ons

Shoes that slip easily on and off are ideal for dressing room shenanigans. If you want to wear boots, I suggest a version like these with a cheating zipper rather than a true combat boot so you don’t have to mess with the laces. If you’re trying on dresses and need a heel, ask to borrow a pair or bring your own (especially if you have a specific pair in mind that you want to wear with the dress). My absolute favorite dressing room shoe is a loafer or ballet flat because they’re comfortable to walk in and don’t require bending down.


Bring your own bags! I like to shop with a small handbag stuffed with one small and one XL Baggu or convertible bag. Doing so means I A) won’t waste paper or plastic if I buy something B) can keep my purchases compact, and C) can sling whatever I’m toting over my shoulder when I’m done instead of dealing with the inevitable palm digging scenario cultivated by a classic shopping bag.

What’s your go-to outfit when you know you’re going to be trying stuff on? I want to hear your tricks too.

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