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 at Who What Wear, currently leading the market team to deliver highly covetable and convertible content. He creates data-driven shopping guides featuring top retailers like Nordstrom, Shopbop, and Net-a-Porter and is at the forefront of Who What Wear'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.
-
Hold the Basic Jeans—This "Dated" Denim Trend Is on Its Way Back
Get ready for this comeback.
-
24 Chic Under-$100 Nordstrom Anniversary Sale Finds That Are Taking Over My Fashion-Editor Text Group
Longchamp, Levi's, Madewell, and more.
-
I Swear By Elegant Outfits—35 Standout Items That Would Fit Right Into My Closet
Here's to a chicer outfit rotation.
-
Too Hot to Think? Try These 33 Chic Summer Finds From Revolve That Basically Style Themselves
Matching sets and lovely lace styles.
-
This Is the Sofia Coppola Way to Style Jeans for Summer
We're beguiled.
-
Low-Rise Jeans and Ballet Flats Look Dated Compared to This Trending Jeans-and-Sneaker Combo
Confirmed by Dakota Johnson and Natalie Portman.
-
Linens, Trousers, and Button-Downs, Oh My! These 30 Banana Republic Sale Picks Are Summer Magic
Up to 60% off.
-
If You Hate Denim Shorts, It's Because You're Not Styling Them With *This* Fresh and Sophisticated Shoe Trend
Hold the sneakers.