How to Wear Leggings

• Part of our How to Wear It series •

How to Wear Leggings in 2021, 22 Different Ways

by Madeline Berger
January 8, 2021

You’ve probably owned leggings in some form or another since your adolescence. People across the world have pondered how to wear leggings for a long, long time. They’ve swung in and out of fashion since 14th century Scotland (really!) and were purely a menswear trend through the 19th century. Cuties like Audrey Hepburn helped popularize slim cropped pants in the ’50s, and by the ’60s, spandex existed and the state of bottoms was never the same. You’ve probably been privy to the are-leggings-pants-or-NOT?! argument at some point and strongly encouraged to wear them only with tops that stretch well past your waist for modesty’s sake.

So, what are the rules for how to wear leggings in 2021? Surprise: there are none! With leggings coming in more fabrics and styles than ever, the world of stretchy, body-hugging bottoms is bigger and better than our elementary school selves could have imagined. So whether you own classic black leggings, faux leather, printed, or other, we’ve rounded up 22 ways to wear leggings from across the web and around the globe.

Credit: Maria Ines Ariani

A subtle snakeskin print on leggings is a perfect texture pairing with an oversized sweater in a swinging, poncho cut. The contrasting fabrics add a punch of wowza and is the perfect mix of cozy and cool.

Credit: Samantha Mariko

We loved Samantha’s look the moment we saw it—a colorful sweatshirt, oversized denim jacket, and fanny pack are the perfect accessories for this sporty, ’80s-inspired look.

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Credit: Andy Yanata

A show-stopping look for Hong Kong’s fashion week, Andy wears an oversized structured top and jacket. The wide brimmed hat adds to the drama, while leggings keep the look focused on the voluminous upper pieces.

Credit: Claudia Villanueva

There’s nothing like the classic combination of leggings and an oversized hoodie. Claudia pairs a leopard print with a graphic hoodie and platform boots for a twist!

Credit: Jessie Bee

Jessie’s look takes an obvious outfit for leggings and manages to make it look absolutely cool. The marmalade longline tank and sneakers add coordination that make this look perfect for a drink on the patio.

Credit: Natalie Borton

On her blog, Natalie spends a full week styling a simple pair of black leggings. The looks are clean and simple like this one, where mule loafers and a popped collar under a navy crewneck add a bit of prep to a basic look.

Credit: Inwon Lee

Leggings barely peek out under doubled-up long coats in contrasting colors. Bright sneakers and reflective sunglasses add a punch to an otherwise b&w outfit.

Credit: PAMELA

A romantic black and white dress is given a bit of edge by Pamela—she pairs it with faux leather leggings and stilleto-heeled boots for a sharp twist that’s ready for dinner or dancin’ the night away.

Credit: Caro Daur

Leggings are perfect for a longer statement coat like this one on Caro. With a much shorter front, you get leg from the front and a covered backside.

Credit: Andrea Funk

Matching sets are everywhere since staying home became the thing and getting dressed felt increasingly like a chore. This cute set was made street-ready by throwing on a jacket and platform sneakers.

Credit: Vita Chen

The ultimate cool-girl look? A pair of pleather leggings paired with a matching bralette and moto jacket—the round sunglasses and beret add a hint of romance!

Credit: Jon The Gold

Jon the Gold is one of our favorites on Lookbook, and for good reason. The matching leggings and shorts add an exciting street style feel to a long-sleeve tee and combat boots.

Credit: Eglė Jasiukaitytė

Eglé is the epitome of cool with classic Adidas leggings paired with cherry red Doc Martens and an absolutely fabulous fur coat. The beanie up top adds a playful, punkish detail perfect for roaming the city by bike.

Credit: Arus Ssah

Arus describes her look perfectly—”Cute and comfy. Sporty yet put together”. By sticking to a neutral color palette throughout, her casual pieces look clean and polished.

Credit: Miamiyu K

An absolutely cozy look featuring grey leggings and a sweater dress with bold stripes. A beanie and sneakers keeps the look fun and casual.

Credit: Kristen Tanabe

Kristin goes glam with black leggings base under a translucent tulle skirt in the same color. A long, bright blazer and statement belt make this one heck of a look.

Credit: PJ Chen

Black leggings let the top half of PJ’s outfit take center stage—a red and black striped shirt packs a powerful punch when paired with a red flannel and coordinating bag.

Credit: Luna Tiger

A golden chenille sweater is at the center of this look, with satin shorts and a printed button up adding playful elements underneath. The leggings are a fun alternative to tights that add a peek of ankle before you hit the boots!

Credit: Edgar

Edgar stays sporty with an outfit anchored by graphic lines and strong contrast. His jersey-inspired tee is the centerpiece, with black leggings under white shorts adding stark chunks of color blocking below.

Credit: Jelena

Jelena goes classic and casual with a hip-length mock neck sweater and oversized denim jacket. Minimal sneakers keep a casual feel and the overall look balanced.

Credit: Kay Lai

Look absolutely chic by pairing leggings with backless loafers and an oversized sweater dress, going monochrome from head to toe.

Credit: Life Stalkers

Plaid leggings can be overwhelming, so pair them with a chunky sweater dress and bright coat to keep visual interest running from top to bottom and a cheery holiday flair.

Ready to hit the ground running with new ways to style leggings? If you’re inspired to pick up a new pair, check out our selection of affordable leggings and bike shorts!