Jeans and leggings are wardrobe staples in many of our wardrobes. As a result, the two pieces often make consistent appearances in our weekly rotations. While you may have a few go-to looks you pair with both leggings and jeans, we thought we’d offer up some fresh inspiration if that’s of interest. Specifically, we wanted to focus on shoe pairings.
In reality, just about any footwear silhouette can pair nicely with jeans and leggings. That said, fashion people have been wearing a few key winter shoe styles as of late. With that in mind, we pulled a range of imagery that showcases the shoes that look impossibly chic with leggings and jeans to consider for the season. Keep scrolling for more. Oh, you’ll also uncover inspired shopping picks throughout, including top-notch jeans, leggings, and shoes.
Flat Chunky Boots
Chunky flat boots are one of the key shoe silhouettes of the season, and they look perfect with straight-leg jeans.
Tuck leggings into flat boots for a very modern vibe.
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Knee-High Boots
Knee-high boots and skinny jeans is a combo that just works.
Similar to skinny jeans, knee-high boots also look A+ with leggings. Very into this monochromatic look.
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Ankle Booties
Black booties are a classic choice. They're wildly versatile, and look chic with straight-leg jeans.
Colorful ankle booties pop against leggings for a modern silhouette.
Shop more booties:
Next, check out more leggings outfit ideas.
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My Stylish 56-Year-Old Mom Is a Picky Shopper—31 Chic Under-$100 Nordstrom Finds She Approves OfCollarless blazers, Fair Isle knits, and Levi's jeans inside.
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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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I'm a Gen Zer Who Loves Parisian Fashion—33 Affordable Finds That Give French Cool GirlExpensive-looking cardigans and elegant winter coats ahead.
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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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I Just Introduced My 56-Year-Old Mom to Revolve—37 Cyber Monday Deals She and I Agree OnExpensive-looking winter finds ahead.
