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.
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Next, check out more leggings outfit ideas.
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Summer or Fall, This Is the Casual But Elegant Flat-Shoe Trend That Always Looks Good With JeansAs seen on Jennifer Aniston.
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Spotted on Zoë Kravitz on a Stroll With Harry Styles: Fall 2025's It-Girl Denim TrendTheir style is already in sync.
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There's No Question—These 8 Fall Shoe Trends Will Make You Look RichLuxe outfits are in your future.
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It's Official: This Is the Flat-Shoe Trend to Wear With Fall 2025's Most Popular Legging ColorAs seen in Los Angeles.
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The Numbers Don't Lie: This Is the Only Denim Trend More Popular Than Baggy Jeans Right NowAccording to data.
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I'm an NYC Shopping Editor—I Can't Stop Thinking About These 31 Rich-Looking Fall Finds FromReplica Store, Zara, and H&MDid I mention they're under $250?
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I'm 5'0"—These Are the Only Jeans That Get My Petite ApprovalThe hunt is over.
