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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If You’re Going to Wear Leggings in Fall 2025, Wear Them in This Shade with White SneakersAs spotted on Jennifer Lopez in NYC.
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Fashion People With Good Taste Are Obsessed With These Trendy Denim Styles for Fall 2025See the outfit inspo and shop the jeans.
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Everyone in Paris Just Ditched Ankle Boots for This Boot Style That’s Way More ElegantAnd super sexy.
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Black Leggings are Fine, But It Girls Know These 6 Trendier Versions Feel So NowThey're so much cooler.
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Bella Hadid Just Landed in Paris Wearing *the* Shoes to Pair With Fall's #1 Denim TrendModel-off-duty elegance to the max.
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*Not* Suede Boots: The Rich-Looking Boot Trend Fashion People Everywhere Are Wearing With Jeans and Skirts for Fall 2025You'll want to add a pair to your rotation.
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This Is the NYC Way to Wear the Anti-Trend Jeans Color French Women Are Obsessed WithAs seen on NYC It girl Irina Shayk.
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Yes, Fashion People Are Still Wearing Leggings, But Only This Specific Style (and Not With Sneakers)The comfy-chic pairing we spot on every L.A. and New York It girl.
