Don't Be Afraid to Wear Your Boots Like Kendall Jenner Just Did—It's Cool Now

Summer ended five months ago, and you're probably sick of wearing ankle boots with cropped jeans by now, so we're here to alert you to a cool new look to try instead for the remainder of winter. We've been noticing that lately, more and more fashion insiders are wearing mid-calf or knee-high boots with jeans and pants tucked into them. It makes for quite an '80s look, which is in keeping with so many trends this season.
Kendall Jenner seems to have noticed this as well, as she just stepped out in Los Angeles right before leaving for NYFW wearing an oversize sweatshirt and Adidas track pants tucked into a pair of white Western boots. On paper, it sounds crazy, but seeing Jenner pull it off may just make you want to give your ankle boots and sneakers a rest next time you wear non-skinny jeans or pants.
Keep scrolling to see how Jenner and other chic fashion insiders are wearing their boots now, and shop boots similar to Jenner's.
On Kendall Jenner: Adidas pants; R13 boots
Shop Similar Boots
Next up, the photogenic trick Kendall Jenner uses in every picture.

Allyson is a senior editor for Who What Wear. She joined the company in 2014 as co-founder Katherine Power's executive assistant and over the years has written hundreds of stories for Who What Wear. Prior to her career in fashion, Allyson worked in the entertainment industry at companies such as Sony Pictures Television. Allyson is now based in Raleigh, North Carolina, and is originally from Baton Rouge, Louisiana. She holds a BFA in theater arts. Her path to fashion may not have been linear, but based on the number of fashion magazines she collected as a child and young adult, it was meant to be.
-
The Specific Way Everyone Stylish in NYC Will Be Wearing Boots With Jeans This Fall
It's all about this styling trick.
-
This Dated Denim Pairing Is Suddenly the Chicest Way to Wear Jeans for Fall 2025
Easy and stylish.
-
If You Want to Fit In With Fashion People This Fall, Swap Your Basic Crewnecks for This Right-Now Alt
The girls that get it, get it.
-
I'm an NYC-Based Dad Who Is Always on the Move—This Is How I Redefined My Everyday Wear
Effortless, easy, and cool.
-
Here They Are: The 6 Biggest Boot Trends of Fall 2025
Exotic finishes! Sock boots! Western motifs!
-
Ignore the Haters—I Still Love These Versatile and Comfy Pants and Bet You Do Too
See how fashion people from NYC to Paris to London wear them for fall.
-
This Classic Shoe Is Every Parisian's Secret to Making Jeans Look Elevated in Fall
And you probably already own it.
-
There's No Question—These 8 Fall Shoe Trends Will Make You Look Rich
Luxe outfits are in your future.