A Close Reading Of Kendall, Kylie & Hailey’s Aspen Street Style

January is the slowest time for both social events and celebrity news, but thanks to the paparazzi, we’re getting a dose of winter street style all the way from Aspen. Many stars head to the capital of American après-ski (and snow polo) for a little R&R — and a place to show off their covetable fur-coat collections. Sisters Kylie and Kendall Jenner joined Hailey Bieber and friends in the ritzy Colorado ski town for some BFF time on and off the slopes. As 2024 proved, the fur coat is the must-have item of the moment, and all three girlies showed off how they style their shearlings. (It’s pretty aligned with what we predicted slope style would look like for the 2024–5 season.)

Below, we’ve named the archetypes each woman embodies with their style. They all have distinct flairs and stylistic personalities, despite all wearing the same teeny black sunglasses. Keep reading to get a few pointers on how to channel their energy as we trudge through the winter.

Kendall: The Vintage Darling

Kendall’s street style of late is a who’s who of collector’s vintage. One minute, she’s sizzling in secondhand Alaïa, the next she’s in museum-quality Thierry Mugler. She’s leaned full force into the nipped-waist blazers popular in the late ‘80s, as further evidenced by this trio of cinched looks. The first stars the divisive celebrity-fave The Row Margaux bag, alongside a sumptuous Cossack hat and an hourglass blazer. The second and third looks show off her curatorial eye, with a Tom Ford for Gucci black fur-trimmed jacket and a Balenciaga Fall/Winter 2011 fox coat, respectively. A few notes: Simplicity is key here, especially if you’ve coughed up a band or two for your limited-quantity outerwear. Also, consider investing in a hat that isn’t a beanie this winter.

Hailey: The City Tomboy

We’ve previously documented Bieber’s casual-yet-runway-ready style that leans the most into “cool dad” out of this trio, and in Aspen she kept it equally relaxed. For a coffee run, she wore a floor-length Ralph Lauren fur from the ‘90s with some blue jeans and a Yankees hat, bringing some Upper East Side flair to her après ski. She kept on the denim and hat and paired them with loafers and Saint Laurent biker jacket, and for dinner, she went full mob-boss mode in a larger-than-necessary Ferragamo fur coat. Where Kendall is all about waist and legs, Hailey is all about covering up in the name of being mysterious — and staying prepared for wind gusts. She also shows real fur, when taken care of correctly, can be sustainable and last almost 30 years.

Kylie: The Indie-Brand Fiend

While Kendall and Hailey are pulling from the archives for the deepest cuts possible, Kylie is perusing her Instagram explore page in search of exciting new talent. The jacket she paired with rigid denim and celeb-fave The Row loafers is from Darkpark, a Milan-based independent label making roomy denim and unique outerwear since 2021. (Naturally, the $2,000 belted jacket is sold out.) For dinner at Casa Tua, she wore some more fur and black tights, taking cues from the Acne Studios Fall/Winter 2024 runway. Make like Kylie and support an emerging designer, belt-cum-tail or not, and when in doubt (like we’ve said before), wear all black at night.