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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Step Away From the Black Leggings—This Is the Low-Key Legging Color Trend You'll See Everywhere This SummerJennifer Lopez approved.
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Goodbye, Boring Basics—This Is the Elegant Trend New Yorkers Are Wearing With Tank Tops This SummerObsessed.
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It's Settled: This Is the #1 Sneaker Trend to Wear With Leggings This SummerConfirmed by Dakota Johnson.
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3 Aesthetic Pairings to Try If Your Wardrobe's Starting to Feel StaleFoolproof solutions.
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I Can't Stand It When People Follow These Fashion Rules to a TIt's time to break the rules.
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10 Style Tips That Will Make You Look Rich This SummerNumber four is already trending.
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Brand Layering: The Art of Knowing Which Labels to Pair With Each OtherThe ultimate styling hack.
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The Simple Styling Trick That Turns Pencil Skirts From Corporate to Chic in 5 Seconds or LessIt's completely free and ready to copy.
