When in Aspen, stylish Angelenos wear leggings in one way and one way only: tucked into riding boots. Sorry, but it's just a fact. If you know what's good for you, you'll follow suit, even if you're not headed to Kemo Sabe, Betula, or Ajax. Why? Because Kendall Jenner said so. She styled her go-to pair of Commando Classic Leggings in the most elegant, non-sporty way while spending the long weekend with Hailey Bieber and Fai Khadra in Colorado's chicest winter ski destination.
Jenner was spotted grabbing coffee with her two close friends in Aspen's downtown district wearing her leggings tucked into a cool (and very fitting for the locale) pair of Ann Demeulemeester's Nes Riding Boots. She layered a black, hourglass-shaped Alaïa blazer on top of a matching turtleneck before finishing off the ensemble with a brown fur cap, sunglasses, leather gloves, and a brown version of The Row's Idaho Tote.
On Kendall Jenner: Alaïa blazer; The Row bag; Ann Demeulemeester boots; Commando Classic Leggings ($108)
For a long time there, the only shoes anyone was wearing with leggings were sneakers, utilizing them solely for fitness-related activities. However, the tides are turning, particularly with A-list dressers like Jenner and Bieber, who recently styled leggings with Mary Jane ballet flats. For colder climates, though, there's only one solid choice of shoes to wear with leggings, and riding boots are it—period.
Scroll down to shop the once-dated outfit combo going viral right now because of Jenner's Aspen street style.
Shop leggings and riding boots:
-
Hailey and Kendall Just Wore the "Dated" Shoe Trend New Yorkers Actually Wear All the TimeI need a pair ASAP.
-
Kaia Gerber Just Wore the Shoes That Always Look Good With Straight-Leg JeansGigi Hadid is a fan, too.
-
Scandi Girls are All About These 6 Minimalist Coat Trends This WinterEven in sub-zero temps.
-
24 Incredibly Chic On-Sale Sweaters and Jeans to Mix and Match From J.Crew, Madewell, and AbercrombieBring on the cool winter outfits.
-
J.Law Just Wore the Casual Pant Trend Fashion People Will Be Wearing Instead of Leggings This YearStyle them with sneakers or flats.
-
I Live in Brooklyn and Am Sure This Is the Only Coat Trend New Yorkers Will Wear Until SpringI see it everywhere I go.
-
Sorry, Barrel Jeans—I Am Forever Loyal to This Classic, Effortless Denim StyleFive chic winter outfit ideas right this way.
-
After All These Years, I'm Still in Love With Hailey Bieber's Style—6 Recent Outfits I'm Copying in 2025Let me reapply my Rhode lip gloss first.
