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.
-
I Live in NYC—These Are the 5 Essential Pieces I Rely On Every Fall
My favorite.
-
No, Really—This Denim Color Is Easier to Style Than Blue *and* Black Jeans
And everyone with taste is wearing it with loafers for fall.
-
It's Controversial (I Know), But Frequent Fashion Flyers Swear By This Jeans Outfit for Long Flights
It involves an elegant leather coat and chic luggage.
-
Taylor Swift Just Wore the Skirt-and-Boots Combo That Screams '90s Jennifer Aniston
It's foolproof.
-
6 Fall Outfit Formulas I'm Stealing From Zoë Kravitz
Effortless, polished, and sophisticated.
-
Sure, Black Leggings Are Timeless, But This Colored Alt Is What Fashion People Are *Actually* Wearing in 2025
Kendall Jenner approves.
-
We Love You, Chocolate Brown, But This Is the Rich Bag Color Trend It Girls Are Wearing Now
Spotted on Ayo and Kendall at the Chanel show.
-
Just so You Know, These Are the Cult-Favorite Hailey Bieber–Approved Jeans Every Celeb Is Wearing
Spotted on Kendall Jenner and Dakota Johnson, too.