As I spent time scrolling through my Saved folder on Instagram, I noticed a pattern. Yes, many of the looks I noted featured leggings as the key piece. It makes perfect sense given that the fashion crowd has been turning to leggings as a go-to elevated basic over the seasons.
Below, I’m sharing the outfits that I think are particularly chic and showcase leggings styled in a forward way. You’ll notice a smattering of ensembles that run the gamut. This includes everything from more dressed-up looks with pieces like a tailored blazer and boots to casual ensembles with a moto jacket and sneakers.
Keep scrolling for outfit inspiration, complete with shopping recommendations as well.
This layered look is easy yet feels high-concept with the cardigan-and-tee combo underneath the longline jacket. The pair of leggings and booties pairing is also to note.
Talk about a chic ensemble with the of-the-moment oversize leather jacket, half-zip sweater, leggings, and chic knee-high boots.
A blazer brings polish to any look, and the sweater tied around the shoulders adds a forward twist.
Need a cool, casual look? Style your leggings with a hoodie and a relaxed puffer with those trusty Uggs.
A moto jacket is no-fail and looks fantastic with everything—including these split-hem leggings.
A popular quilted jacket teamed with leggings and heels? Chic.
Next, check out more items to wear with leggings.
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If Parisians Walked Around in Leggings Like It Girls in NYC and L.A. Do, They'd Choose This Expensive-Looking Color TrendHint: It's not black or brown.
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*Not* Black—6 Legging Color Trends Everyone Everywhere Will Be Wearing in 2026Everything you need to know about wearing leggings next year, all in one place.
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If You're Going to Wear Leggings to the Airport in 2026, Pair Them With This Expensive-Looking ShoeIt's giving aspirational.
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Introducing the Prettiest Legging Color Trend of 2026, as Worn by Maya HawkeBetter than black.
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If You're Going to Wear a Sweater and Sneakers With Leggings This Winter, Choose Them in This Pretty Color TrendJ.Lo knows a good legging hue when she sees one.
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Forget *It* Styles: These Back-to-Basics Sneakers Make Black Leggings Look Cool and ClassicThese shoes have been around for over 15 years.
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Hold the Hoodies and Puffers—L.A. It Girls Are Wearing *This* Anti-Trend Item With LeggingsIf anyone knows a good legging outfit, it's Kaia Gerber.
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Here's How All the Cool Girls Will Be Wearing Their Leggings This WinterThese outfits feel more fashion and less fitness.
