Celebrity Style Aspen: Winter Style Inspo from Kendall, Hailey + Kylie

Photography by Backgrid, courtesy of Simon Miller

Dressing for the cold *and* looking stylish? Say less!

Is it even the holidays if Hollywood royalty isn’t photographed on a lavish trip to Aspen? Each year, like clockwork, the rich and famous escape the L.A. sun for the frostier temps of Colorado’s winter wonderland. The swanky ski town has lots to offer: crisp air, snowy slopes, and the opportunity to wear your most outrageously glamorous winter attire. Enter: Hailey Bieber, Kendall Jenner and Kylie Jenner.

The trio of famous besties closed out 2022 with a trip to Colorado’s Rocky Mountains, where they proved their renowned street style prowess can adapt to any weather condition. The evidence? A seemingly endless supply of shearling fuzzy coats, outsized footwear, and versatile yet avant-garde accessories.

Kylie Jenner, specifically, went viral for bringing edginess to the polished après-ski aesthetic. As of late, many of the beauty mogul’s looks — which are now reportedly being styled by sisters Alexandra and Mackenzie Grandquist — have come straight from exclusive fashion archives. Case in point: the 1987 vintage Alaïa shearling jacket she wore on December 30. Jenner sported the coat as a dress (naturally!) and paired it with sheer stockings, Maison Margiela leather boots and a fuzzy black bucket hat.

Looking this chic in chilly conditions is no small feat. Hailey Bieber’s trick? Head-to-toe neutrals. The model, whose stylist Dani Michelle is a master at concocting trendy looks, wore all-black-everything on December 31 with a wool trench, tiny sunglasses and a handbag, all by Saint Laurent. To complete the cozy look, she wore a pair of puffy Loewe boots. But that’s not to say Bieber didn’t also dress up.

Hailey Bieber Aspen
Photography courtesy of Saint Laurent

Earlier on the trip, Kendall Jenner and Bieber went out to dinner with two decidedly different approaches to a night out in the cold. Jenner opted for a ’90s-style red maxi dress, a leather trench and a giant fuzzy green scarf that could easily double as a blanket. Bieber, on the other hand, made a convincing case for the season-less miniskirt. Holding hands with her husband Justin Bieber, the model sported a tonal brown Maximilian Davis skirt set lined with fur. Her footwear of choice for the outing? A pair of shaggy knee-high white boots. This brings us to a defining trend of the trip: fuzzy footwear.

On New Year’s Day, Kendall served Yeti chic in a pair of furry cowboy boots by R13 (which promptly sold out). To tie the wintery Westernwear look together, she donned a Simon Miller coat and a fringe-adorned handbag. Alongside her, Kylie Jenner sported yet another shearling jacket, this time an oversized style from Acne Studios, with baggy cargo pants and a Hodakova Buckle Belt shoulder bag. You may be wondering: how many shearling coats are too many? As Mean Girls’ Cady Heron once said: the limit does not exist.

But the pièce de résistance among this vacation sartorial splendour? The outfits from New Year’s Eve, of course. To bid 2022 adieu, Bieber once again went monochromatic in a large wool trench atop a black tube top and matching miniskirt (shocker!). In the spirit of honing in on what you do best, she paired the ensemble with a Hailey Bieber staple: sheer tights, this time by Calzedonia.

Hailey Bieber Aspen NYE 2022
Photography by @jbtmedia, courtesy of Calzedonia

To close out the year, the Jenner sisters synchronized in sultry catsuits topped with statement-making overcoats. Kendall donned an opaque one-piece with a bright orange tiger-print coat, while Kylie modelled a plunging fishnet suit from Alaïa with a glossy gargantuan fur jacket. If there’s one thing we can glean from this medley of glamorous get-ups, it’s that snow should be no deterrent for having fun with your style. ‘Til next year, Aspen.

Feeling inspired to infuse some celeb-level experimentation into your winter 2023 wardrobe? We’ve got you covered. From fuzzy parkas and unconventional footwear to the perfect oversized chapeau, you can channel your ski vacation alter ego, no plane (or lift) ticket required.

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