Kendall Jenner and Hailey Bieber Style Polar-Opposite Après Ski Outfits—and 2025 Shoe Trends—for an Aspen Coffee Run

Lest you thought après-ski outfits were all cable-knit sweaters and fur-lined boots, Kendall Jenner and Hailey Bieber are here to set the record straight.

The best friends have been making Aspen their runway over the past week, interspersing blizzard-friendly puffer jackets and ski pants for double-black diamond runs with luxury black dresses and fur coats for taking over the town square afterward. In the spirit of the best celebrity couple outfits, these tight-knit friends (and their stylists) interpret the post-lift dress code in dramatically different ways. From their personality hats to the winter 2025 shoe trends on their feet, they couldn't have more opposite interpretations of slope style.

First, there's Kendall Jenner. Last winter, she told me in a Harper's Bazaar interview that The Row was the "obvious" designer to wear in a ski town. She doubled-down on her proclamation a year later, grounding a sculpted Alaïa blazer coat and vintage fur hat sourced from A Part of the Rest with The Row's leather Idaho tote. She walked the slushy sidewalks in a pair of Ann Demeulemeester riding boots, a hat-tip to her equestrian hobby and the runways' recent obsession with countryside style. Black Commando tights, oval sunglasses, and leather gloves put a finishing gloss on her outfit—one that conveyed rich-girl energy with every stitch.

While she shares a stylist in Michelle, Hailey Bieber took a completely opposite route—one that was less Swiss chalet and more downtown New York. The Rhode founder tapped into all her day-to-day signatures, ditching the vintage fur coat she wore earlier on the trip for a Saint Laurent leather bomber jacket, straight-leg jeans, and a Yankees baseball cap.

Her footwear, while tuned-in to the runway's preppy side, was also the opposite of Jenner's. She instead chose a pair of The Row's "Boyfriend" loafers, a sophisticated twist on the boat shoe trend set to dominate spring 2025.

Kendall Jenner and Hailey Bieber have more in common than their outfits imply on the surface. They're both business moguls and models, and they're both willing to pack their favorite designers for a trip up the mountain. (Bieber is a longtime devotee to Saint Laurent's bags, coats, and shoes; Jenner, meanwhile, has a thing for copy and pasting entire looks from The Row's runway.) Maybe these après ski outfits and associated shoe trends are just saying the same thing in a different font: You don't have to dress like someone else on vacation.