The 6 Shoes You Should Own If You Live in Leggings

I’ve been getting dressed up on occasion for a bit of mood-boosting fashion, but often, I’m wearing many of the comfortable pieces in my closet on rotation. That means everything from my favorite sweatsuit sets to loungewear to leggings. More and more, I’ve seen that leggings are a mainstay in the wardrobes of fashion insiders and I’ve noticed all of the cool, sophisticated ways they’re wearing them, which has made me think about new ways I can style my own—and it seems like shoes are an interesting place to start.

When pairing shoes with leggings, they can really transform a basic pair of black leggings. Yep, if you’re wearing anything from athletic sneakers to knee-high boots to heels, there’s always a fashion-forward way to pull them off. Ahead, I’m highlighting 6 key shoes to own if you want to take your leggings beyond a workout and I promise you’ll never think about the closet staple the same way again.

Athletic Sneakers


(Image credit: @pernilleteisbaek)

Pictured: Totême jacket; Wardrobe.NYC leggings; Acne Panelled Suede and Mesh Trainers ($410)

Styling tip to borrow: Add a simple T-shirt and leather blazer to instantly elevate an outfit with leggings and sneakers.

Shop the shoes:



(Image credit: @leiasfez)

Pictured: Zara Ottoman Leggings ($30)

Styling lesson to borrow: If you're looking for a Zoom-ready look, this is one to copy. Nothing is better than pairing a button-down top with comfortable leggings and loafers.

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Sleek Pumps


(Image credit: Courtesy of Moda Operandi; Photographed by Heather Hazzan)

Pictured: Jacquemus jacket; Bottega Veneta Quilted Leather Pumps $1100

Styling tip to borrow: Opt for a pair of split leggings, which have the look of tailored pants. Then, add a blazer, earrings, and chain bracelet for a sophisticated take on leggings.

Shop the shoes:

Flat Knee-High Boots


(Image credit: @camillecharriere)

Pictured: Prada jacket; Coccinelle bag; Ann Demeulemeester boots

Styling tip to borrow: Add a turtleneck and structured blazer to your leggings and flat knee-high boots to replicate this outfit. You probably have most of these pieces sitting in your closet already.

Shop the shoes:



(Image credit: @tylynnnguyen)

Pictured: The Row sweater; Totême leggings; Hunting Season bag

Styling tip to borrow: Keep things simple by pairing a loose sweater and cap with your leggings and sandals. This is the ultimate chic cozy look.

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Colorful Heels


(Image credit: @annarvitiello)

Pictured: Chanel jacket; Totême leggings; Amina Muaddi Gilda Embellished Leather Mules ($1020)

Styling tip to borrow: Wear a colorful jacket and heels to offset a basic pair of black leggings. Try sticking to the same color family for a slightly tonal look.

Shop the shoes:

Next, shop 25 cool fashion finds I’m obsessing over right now.

This post was previously published and has since been updated. 

Associate Director, Special Projects

Kristen Nichols is the Associate Director, Special Projects at Who What Wear with over a decade of experience in fashion, editorial, and publishing. She oversees luxury content and wedding features, and covers fashion within the luxury market, runway reporting, shopping features, trends, and interviews with leading industry experts. She also contributes to podcast recordings, social media, and branded content initiatives. Kristen has worked with brands including Prada, Chanel, MyTheresa, and Luisa Via Roma, and rising designers such as Refine and Tove, and her style has been featured in publications including, Vogue France, WWD, and the CFDA. Before Who What Wear, Kristen began her career at Rodarte, where she worked on assistant styling, photo shoots, and runway shows, and at Allure, where she moved into print and digital editorial. She graduated from the University of Southern California, where she studied art history and business, and currently lives in New York.