5 Chic Ways Celebs Are Wearing Their Basic Leggings This Winter

This winter, leggings have officially leveled up, and I'm here for it. If you've ever struggled to make leggings look anything other than lazy, you're not alone. Luckily for us, It girls like Bella Hadid, Kendall Jenner, and Hailey Bieber are showing us how to make leggings look cool—not sloppy—this season. The trick? Think outside the basic socks-and-sneaker combination that's often the go-to for many. Hadid has been pairing her leggings with stylish puffer jackets and '80s-inspired headbands, and Jenner is opting for the model touch with tailored tops and unexpected footwear. These celebs are making it clear: When styled the right way, leggings are anything but basic.
If you've been caught in the struggle of elevating your legging game this winter, take notes from these fashion icons. A little creativity (and a killer coat) can go a long way and make this cold-weather staple work overtime in your wardrobe, even when temps are below freezing. Below, scroll through our five favorite celebrity-approved legging outfits.
With Furs
WHO: Hailey Bieber
Leave it to Mrs. Bieber to give the girls exactly what they want. The Rhode founder stepped out in a luxurious fur coat layered atop of leggings, the ultimate comfort-first pant choice. High-heeled, knee-high boots completed the look, proving leggings don't have to be reserved for the gym and late-night errands.
With Hot Pants
WHO: Jodie Turner-Smith
Leggings don't have to just be black, basic, and (sometimes) boring. Jodie Turner-Smith stepped out in an arctic-white pair layered underneath hot pants, a black boatneck tee, and a matching wool coat. Black classic pumps completed the look, instantly transforming leggings from a chill-day outfit into a look perfect for going out in.
With Puffer Jackets
WHO: Bella Hadid
Leave it to Hadid to inspire us to wear our athleisure outside of the house again this winter. Paired with a puffer jacket, workout jacket and thick '80s-inspired cotton headband, the model's leggings are peak functionality for her look. Her riding boots, though, take these leggings from post-workout to full-fledged 'fit, adding an unexpected layer and playing on the wrong-shoe theory.
With Riding Boots
WHO: Kendall Jenner
Take a page from Jenner's book—the model opted to wear her standard black leggings with a cropped wool coat, black leather gloves, and a fur-trimmed hat for a slopeside serve. Much like Hadid, the addition of riding boots in lieu of running shoes makes the leggings feel more fashion than fitness.
With Shackets
WHO: Tate McRae
If you're looking for a transitional outfit in the later winter months, opt for a long, felted shacket over a bulky winter coat and leggings. Sleek, streetwear-inspired orange-lens sunglasses are also an instant way to elevate your outfit.

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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