The Jenner's & Hailey Bieber’s Vacation In Aspen Was An Aprés-Ski Lover’s Dream

Each winter, the question isn’t if celebrities will vacation in Aspen, Colorado, it’s when. Unsurprisingly, this season is no different. Ever since the mountainside city’s first snow-fall in November, Mariah Carey, Bella Hadid, Jennifer Lopez, and Kate Hudson (to name a few A-list visitors) have been spotted in Aspen, wearing chic winter-friendly ‘fits both on and off the ski lift. And most recently, Hailey Bieber, Kendall, and Kylie Jenner got in on the fashion-forward fun. Starting on Jan. 15, the fashion muses met up at various Aspen hotspots in aprés-ski attire from The Row, Gucci, Balenciaga, Ferragamo, Ralph Lauren, and more.

Kendall and Bieber were the first to arrive in the snowy scape. Bright and early on Wednesday morning, the models were snapped by the paparazzi on a stylish coffee run. Kendall, for one, looked timeless in a peplum-esque blazer coat from Alaïa, alongside an oversized The Row clutch and a vintage fur hat. Bieber, on the other hand, didn’t stray too far from her L.A.-ready wardrobe. The Rhode Skin founder went a more casual route in a baggy Saint Laurent bomber jacket with mid-wash jeans. Contrary to Kendall’s elevated accents, the new mom accessorized with a baseball cap, The Row loafers, and slim sunglasses — some of her street style staples.

A few days later, on Jan. 18, Kylie jetted into the popular ski destination. That evening, the three convened at Casa Tua, a popular Italian restaurant in the heart of Aspen. For her first Colorado co-ord, Kylie stunned in an extravagant black shearling coat styled as a dress. Her older sister matched her sartorial energy in a vintage fur-trimmed skirt set from Gucci by Tom Ford Fall/Winter 1996. In true It girl form, Bieber also got the fur memo in a floor-length multicolor topper, courtesy of Ferragamo Resort 2025.

But wait — there’s more. Keep scrolling for all the luxe looks worn by Kendall, Kylie, and Bieber on their Aspen getaway. Spoiler: Each outfit outdid the last.

January 15

For an early-morning coffee run, Kendall and her stylist, Molly Dickson (whom Bieber also works with), secured a fit-and-flare blazer coat from Alaïa — one of her go-to ateliers both on and off the red carpet. From there, the 818 founder tucked a pair of black Commando leggings into knee-high boots from Ann Demeulemeester. She upped the cool-girl vibes with The Row’s Idaho Bag in a dark chocolate color-way. Then, she braced for the chill in a striking fur hat sourced from A Part of the Rest, a San Diego-based vintage studio.

Despite the freezing temps, Bieber opted for some of her signature pieces, starting with an oversized bomber jacket from Saint Laurent, and straight-leg jeans. Underneath her denim bottoms peeked The Row leather loafers: another Bieber classic. A baseball cap, a Saint Laurent tote bag, and slim oval-shaped sunglasses completed her OOTD.

January 16

During a solo evening out at Matsuhisa, a top-tier sushi restaurant, Kendall was photographed in black trousers, pointy ankle boots, and a French girl-inspired beret — all of which complemented her beige Balenciaga fur coat.

January 17

While out with her husband, Bieber tapped into her signature outfit formula again. This time, she wore light-wash low-rise jeans, a vintage Ralph Lauren Fall/Winter 1995 oversized coat, Miu Miu’s Aventure Bag, and monogrammed Gucci sunglasses. The New York Yankees baseball cap finished her ‘fit once more.

January 18

After the grand GNO, Kylie offered photographers a close-up of her enviable ensemble, complete with a furry black coat, pointy pumps, and Gucci oval-shaped sunglasses.

Marking her latest archival look, Kendall got her hands on a matching skirt set from Tom Ford’s Gucci Fall/Winter 1996 collection. The suede two-piece featured a fur trim along the neckline, the bodice, and the skirt’s hem.

Bieber went full mob-wife mode in this maximalist fur coat from Ferragamo Resort 2025. She upped the loud luxury vibes with patent leather knee-high boots and round sunglasses.

January 20

On Monday morning, all eyes were on the Jenner sisters outside the Little Nell Hotel restaurant. The dynamic duo subtly coordinated for the lunchtime jaunt in fur coats. Kendall led the way in leather trousers, which looked sleek next to her plain white T-shirt and cool-toned topper. Kylie followed suit in a cropped jacket, covered in tan shearling. Then, she took cues from Bieber with The Row loafers and oval-shaped shades.