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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I'm a Fashion Editor—These Are the Low-Key Uggs I'll Be Wearing With Leggings All Winter LongI just bought my first pair of Uggs.
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Listen, Being Cool in 2025 Requires Just Two Things: Loose Jeans and This “Weird” Viral Flat-Shoe TrendThey're strange, but so chic.
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My Mom Is in Her 50s and Asked Me for Fashion Advice—8 ChicReplica Store Outfits I Put Together for Her Under $425Outdated prints and "ugly" shoes included.
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These Easy Outfit Formulas Make Even Fall's Most Polarizing Boot Trend Look CoolSee the inspiration inside.
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This Is the Luxe Fall Shoe Trend Every Fashion Person Is Already Wearing on RepeatCount these inspo pics as proof.
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No, Really—This Denim Color Is Easier to Style Than Blue *and* Black JeansAnd everyone with taste is wearing it with loafers for fall.
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From Sweden to London: The Surprising Jeans Color European Fashion People Are Reaching for This FallHere's how to pull it off.
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It's Controversial (I Know), But Frequent Fashion Flyers Swear By This Jeans Outfit for Long FlightsIt involves an elegant leather coat and chic luggage.
