What Not to Wear With Leggings in 2023, According to an Editor

I'm not sure if you've heard, but leggings are actually trendy again. They're a staple, so they're never really "out," but wearing them to places besides workout classes has become cool again—because fashion is cyclical. Leggings can be a tricky article of clothing to style. But given how comfortable and cool they have the potential of being, I'd say that putting a little extra thought into your legging outfit is worth the effort, and that includes considering what not to wear with leggings.

At this point, given the fact that leggings became a wardrobe staple years ago, we're used to seeing celebrities out and about wearing them instead of pants. Celebs repeatedly set stylish examples of how to pull off leggings, and it all depends on what you wear them with. That said, to achieve the most forward look, there are some pieces you may want to skip when donning the staple in 2023.

Ready to become a legging styling master? Read on to find out which seven things to avoid wearing with leggings and, of course, what to wear instead.

Skip: Bodysuits

Wear Instead: Tank Tops

If VPL is something you care about, you may want to avoid bodysuits. Instead, a tank top with leggings will always be the most fail-safe combination there is.


(Image credit: Splash News)

On Olivia Wilde: Gucci bag

Shop Tank Tops

Skip: Going-Out Tops

Wear Instead: Button-Downs

Although it's true that leggings can be dressed up or down, they're essentially an athleisure piece, making a fancy top a less-than-ideal choice. Instead, opt for an oversize button-down, which is a no-brainer with leggings.


(Image credit: BG020/Bauer-Griffin/GC Images)

On Hilary Duff: Bottega Veneta bag

Shop Button-Downs

Skip: Sky-High Heels

Wear Instead: Sneakers, Loafers, Mules, and Boots

While certain heels can work with leggings, they pair best with flats and sportier styles such as sneakers. And yes, the cool-girl way to wear them is still with crew socks.


(Image credit: Backgrid)

On Kendall Jenner: ALO High-Waist Airbrush Leggings ($98); Ugg Tasman Slippers ($110)

Shop Shoes

Skip: Dresses and Skirts

Wear Instead: Tunic Sweaters and Sweatshirts

A dress or skirt over leggings was the go-to look in the '80s and again in the mid-2000s, but it's not one that you'll see much of in the 2020s. This time around, if it's coverage you're seeking, a long, oversize sweater or sweatshirt is a much more modern look. 


(Image credit: Splash News)

On Margot Robbie: Zoe Karssen jacket; Wildfox Couture sweater; Ugg Classic Short Boots ($170); Away The Carry-On Bag ($225)

Shop Tunic Sweaters and Sweatshirts

Skip: Gym Bags

Wear Instead: Handbags

This one may sound a bit odd, but there's a reason celebrities never seem to carry a gym bag when they're going to the gym—an actual handbag is perhaps the easiest way to make leggings streetwear appropriate.


(Image credit: BG020/Bauer-Griffin/GC Images)

On Hailey Bieber: Worn Vintage jacket; TnAction TnaButter Mini Bra Top ($38) and Atmosphere Flare Hi-Rise Leggings ($78); The Row Iris Bag ($1190)

Shop Handbags

Skip: Fitted Blazers

Wear Instead: Oversize Outerwear

Thanks to the magic of playing with proportions, leggings (which are obviously very fitted) look cool with something looser on top, like an oversize blazer or bomber jacket.


(Image credit: TheCelebrityFinder/SplashNews.com)

On Lori Harvey: Loewe jacket; Gymshark Vital Seamless 2.0 Leggings ($54); Bottega Veneta Jodie Mini Bag ($2650); Miu Miu shoes

Shop Oversize Outerwear

Skip: Piled-On Jewelry

Wear Instead: A Few Simple Pieces

Piles of jewelry aren't the best match with the sporty look of leggings. I suggest sticking with subtle, minimal pieces for the most cohesive look.


(Image credit: Bellocqimages/Bauer-Griffin/GC Images)

On Jennifer Lopez: Brunello Cucinelli boots; Hermès bag; Jennifer Fisher earrings

Shop Minimal Jewelry

This post was originally published on an earlier date and has been updated. Next, 7 Ways Every Cool Girl Is Wearing Leggings This Year

Allyson Payer
Senior Editor

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.