Temperatures Down, Leggings On: 7 Elevated Ways to Wear the Cozy-Weather Staple

If there's one thing you can count on to be a universally loved cold-weather staple, it's a simple pair of black leggings. Beloved both by Hailey Bieber and sleepy editors who can't function without their morning coffee after an all-nighter, the chic yet cozy item can feel surprisingly hard to wear, especially if you're looking for an outfit that doesn't resemble pajamas.
Now that fall is kicking into high gear and Ugg-boot season is here, it's only fair to maximize our fresh closets with a timeless pair of black leggings. Trust us—if you style your favorite pair like the fashion people below, no one will suspect you slept in them.
Below, browse some of our favorite fall legging outfit ideas and shop our editors' tried-and-true pairs.
How to style: tank top, wide belt, slingbacks, and leggings
How to style: 2000s-era sunglasses, leather flight jacket, and leggings
How to style: sherpa-lined jacket, knee-high boots, oversize tote, and leggings
How to style: oversize sweatshirt, running shoes, slouchy socks, and leggings
How to style: heeled mules, white T-shirt, tweed jacket, and cropped leggings
How to style: Ugg boots, puffer coat, beanie, and leggings
How to style: riding boots, leggings, oversize blazer, and slouchy sweater

Ana Escalante is an award-winning journalist and Gen Z editor known for her sharp takes on fashion and culture. She’s covered everything from Copenhagen Fashion Week to Roe v. Wade protests as the Editorial Assistant at Glamour after earning her journalism degree at the University of Florida in 2021. At Who What Wear, Ana mixes wit with unapologetic commentary in long-form fashion and beauty content, creating pieces that resonate with a digital-first generation. If it’s smart, snarky, and unexpected, chances are her name’s on it.
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