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.
-
This Simple Fashion-Person Approved Layering Technique Changed the Way I Wear My Basics
Effortlessly cool.
-
Pump the Brakes on Booties—Kate Hudson Knows the Better Fall Shoe Trend to Pair With Dresses
This outfit combo is top-tier.
-
Spotted on Kendall and Hailey: The Pant Color Trend People Are Swapping Blue Jeans For
It girls with good taste know best.
-
Cool It On the Skinny Jeans—Chic People Are Wearing These 6 Fall Denim Trends Instead
Are you taking notes?
-
Jeans, Flats, Jackets, and Sweaters—The Best of the Best In Each Category For Fall
Meet your new hero pieces.
-
Hold the Light-Blue Jeans—People in Paris Know This Denim Trend Is Far Superior for Fall
It's so elegant.
-
I'm Getting a Jumpstart on Fall Shopping—33 Affordable Key Pieces You'd Find In a Wealthy Person's Closet
It girl-approved.
-
Give Your Denim Outfits a Chic Boost With These 21 Jeans From the Madewell Sale
Twenty percent off? Done and done.