As taboo as this may be coming from a fashion girl, I love leggings. They’re my comfortable, go-to pants for running errands, traveling, cold-weather days, and working from home. They can get a bad wrap is because, well, let’s be honest: Leggings are a lazy pick. But I don’t mind a good pair of comfy pants, especially if you can dress them up and style them in ways that take the otherwise glorified cozy pants to a full-on fashion moment.
Our favorite it girls like Kendall Jenner, Bella Hadid, and Hailey Bieber have all had paparazzi shots of each of them featured in leggings, usually leaving a Pilates class or a meeting, officially making leggings cool again. I’ve been eyeing tons of styling inspiration for how to wear leggings all fall and winter long and found four outfits that are so easy to wear and totally elevate a pair you already own.
Keep scrolling to see how I’ll be styling my leggings all season.
Sneakers + Leather Jacket
This is what I would call the cool-girl way to style leggings. The leather blazer makes these leggings look more formal, and the high-top sneakers add a little streetwear edge. Perfect for when you want to be a little more comfy but don’t want to cancel on getting drinks with your friends.
Bra Top + Blazer
Ever wanted to wear a bra top and leggings out and still look put together? Here’s how: Add a blazer, some bling, and your favorite sneakers to dress up the otherwise casual look.
Ugg Boots + Sweatshirt + Jacket
This outfit combination is my go-to for traveling during fall and winter. Not only is it comfortable, but with the right choice of Uggs and sweatshirt, this look can also be super on-trend.
Turtleneck + Baby Tee + Teddy Jacket
How cute is this outfit idea? It definitely gives me Gen Z vibes, but I’m into it. I love the layering aspect paired with a fluffy teddy coat.
Next, check out these shopping guides.
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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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Sure, Black Leggings Are Timeless, But This Colored Alt Is What Fashion People Are *Actually* Wearing in 2025Kendall Jenner approves.
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8 Non-Dated Ways People Are Wearing Leggings Right NowHow to style them the 2025 way.
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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.
