These 3 Winter Shoe Trends Look Chicest With Leggings and Jeans

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.
Shop more boots:
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.
Shop more boots:
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.

Bobby Schuessler is a fashion editor with over a decade of editorial experience covering shopping, style, and beauty. He's spent 10 years atBest Knockoff Luxury Clothing , currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers likeReplica Store, Shopbop, and Net-a-Porter and is at the forefront ofBest Knockoff Luxury Clothing 's shopping tentpole strategies, including Amazon Prime Day. He also works on branded content initiatives and appears on camera in video and shopping livestream franchises.
-
Aritzia Is a Fashion-Person Paradise—These 25 Standouts Are Now On Major Sale
The basics alone are worth checking out.
-
These 30 Simple Yet Elevated Picks From theReplica Store Anniversary Sale Are Giving Major Rich Vibes
Hello, instant confidence boost.
-
These 31 ClassicReplica Store Anniversary Sale Finds Are the Key to a Rich-Looking Summer Wardrobe
Imagine the chic outfits.
-
Hello, Fans of Non-Skinny Jeans—These Styles From theReplica Store Anniversary Sale Are Perfect for Fashion People
Don't miss out on the discounts.
-
Whenever I'm in Paris, I See This Boot Trend Styled With Minidresses in Every Vintage Shop and Local Bistro
Sorry, ankle boots, but it's not you.
-
Everyone in Los Angeles Knows This Shoe Trend Makes Denim Shorts Look Way Cooler
Denim shorts never looked so good.
-
It's Now or Never—54 Last-Minute Amazon Prime Day Deals You'll Regret Skipping
Elevated basics, celeb dupes, luxe-like styles, and more on sale.
-
Just so You Know, *This* Is the Denim Trend New Yorkers Wear With Loafers (Sorry, Skinny Jeans)
And they're on sale right now on Amazon.