The beauty of leggings is that they’re not only versatile, but comfortable. As a result, many fashion people wear leggings to keep comfy when they’re out and about. In terms of the specific outfit formulas that seem to be most popular now, well, style setters happen to be reaching for other cozy items to pair with the equally-comfy leggings.
Below we’re showcasing the comfy yet chic items that work perfectly with leggings. Given that we’re heading deeper into the colder months, a certain chunky knit style is certainly popular. You’ll also notice other go-to relaxed silhouettes. Keep scrolling for a range of styling and shopping inspiration.
Oversize Sweater
A chunky knit is a winter staple, and that ideal style looks perfect with leggings. A pair of crew socks over the leggings is also cool.
Puffer
Puffers are practical (warm!), but also quite chic. This outfit with the vest over the turtleneck and leggings gets an A+.
Utility Jacket
For an effortless silhouette, consider tossing on a utility jacket over a long-sleeve tee with your leggings and ballet flats.
Graphic Sweatshirt
Keep it laid-back yet of the moment with a graphic sweatshirt, leggings, and retro sneakers.
Relaxed Blazer
For an elevated vibe, incorporate a blazer into your legging outfit. To note, it's the relaxed fit of the blazer that will keep the look on the more comfortable side.
Maxi Coat
A roomy coat is another comfortable and chic outerwear pick that looks fantastic with leggings and a sweater.
Next, these are the best leggings, tested by an editor.
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I'm a Fashion Editor—These Are the Low-Key Uggs I'll Be Wearing With Leggings All Winter LongI just bought my first pair of Uggs.
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The Fall Shoe Trend Everyone in Paris Is Wearing With Black Leggings to Runway Shows and Dinners at Chez JanouHint: It's not sneakers or ballet flats.
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Hold the Leggings—This Is What Cool Dressers Are Actually Wearing With Ugg Boots These DaysAs seen on Gigi Hadid, the cool-dresser poster child.
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Forget Fleeces and Hoodies—This Is the It-Girl Jacket to Wear With Plain LeggingsIt's taken over by storm.
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5 Street Style Trends From Milan Fashion Week That Will Be Everywhere This FallTake notes.
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If You're Going to Wear Leggings in Fall 2025, Wear Them in This Shade With White SneakersAs spotted on Jennifer Lopez in NYC.
