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

On January 21, 2025By Littum

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 made Aspen their runway over the past week, mixing blizzard-friendly puffer jackets and ski pants for double-black diamond races with luxe black dresses and fur coats to take on the town square afterward. In the spirit of the best celebrity couple outfits, these close 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.

Hailey Bieber and Kendall Jenner in Aspen — Kendall Jenner and Hailey Bieber walk through downtown Aspen in two very different après ski outfits.

First there’s Kendall Jenner. Last winter she told me in one 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, pairing a sculptural Alaïa blazer coat and a vintage fur hat from A Part of the Rest with The Row’s leather Idaho tote. She walked the sloppy sidewalks in a pair Ann Demeulemeester riding bootsa hat tip to her riding hobby and the runways’ recent obsession with country style. Black Commando tights, oval sunglasses and leather gloves put a finishing touch on her outfit – one that conveyed rich girl energy with every stitch.

Kendall Jenner wears a belted coat from The Row with fur hat and riding boots — Kendall Jenner took a billionaire approach, pairing a vintage fur hat with an Alaïa blazer and riding boots.

Alaïa Archetypes Double Breasted Stretch Gabardine Jacket

Row Idaho Xl leather tote bag

Ann Demeulemeester Nes riding boots

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 made use of all her daily signatures, ditching the vintage fur coat she wore earlier in the trip for a Saint Laurent leather bomber jacket, straight-leg jeans and a Yankees baseball cap.

Her footwear, while tuned to the preppy side of the runway, was also the opposite of Jenner’s. She opted instead for a pair of The Row’s “Boyfriend” loafers, a sophisticated twist on the boat shoe trend set to dominate Spring 2025.

Hailey Bieber wears a bomber jacket with jeans and loafers in Aspen

Hailey Bieber, meanwhile, opted for her casual-cool signatures: a leather jacket, jeans and loafers.

(Image credit: Backgrid)

Saint Laurent oversized jacket in lambskin

Saint Laurent Bea tote bag

The Row Calfskin Tassel Boyfriend Loafers

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