Kendall Jenner Aspen: See Her Best 2023 Looks

Opulent fur coats! Chic skinny sunglasses! Gigantic puffer jackets! Winter style has never looked so good.

If cold-weather dressing is a special skill, Kendall Jenner is a master of the trade. The model has long been marking the start of winter weather with a fashion-filled trip to Aspen, and this year — amid rumours of her split from Bad Bunny — she upped the ante on luxe snow attire.

What does one wear when visiting a ski town known for its heated sidewalks, breathtaking scenery and refreshingly crisp air? For this street style pro, it’s an array of ensembles that reflect the cozy-meets-chic vibe of the Colorado community.

Snapped alongside her besties the Biebers, Jenner had an appropriately wide-ranging wardrobe for her packed schedule. Between hitting the hills and heading to dinner, the creative director of Fwrd also stopped by the boutique’s Aspen pop-up shop to promote the luxury pieces she’s curated.

Through it all, she once again made the case for having fun with fashion amid frostier temps. Below, see Jenner’s best Aspen 2023 getaway looks.

Keeping up with Kylie

While attending the launch of Fwrd’s Aspen pop-up shop, Jenner sported a sleek leather look that felt reminiscent of her sister Kylie’s Khy collection.

The all-black Rick Owens ensemble, which consisted of a belted leather coat and complementary split-hem trousers, perfectly fit the vibe of the new store’s luxurious winter staples. To finish off her look, Jenner wore simple black heels and her long brown hair in effortless loose waves. Perfection!

Sleek pre-slope style

As she strolled through the rocky mountain resort town on Friday afternoon, Kendall Jenner once again showcased the range of her Aspen street style prowess.

The model stayed warm in a cropped glossy Saint Laurent puffer jacket with leggings and fuzzy earmuffs. But the real star of the show? The belted leather splint boots from Rick Owens’ Fall 2023 collection, which emitted straight-from-the-ski-lift coolness.

A luxe oversized fur

For a nighttime outing, Jenner bundled up in an opulent shearling coat from Phoebe Philo’s new highly coveted brand. Coated in a glossy brown hue, the belted fur featured hand-painted black panel detailing throughout.

The model paired the piece (which retails at $27,000 USD, NBD) with a grey-black high-neck top, sheer black tights, glossy dark flats, gold hoop earrings and a leather handbag.

A snow queen serve

On a Saturday dinner outing, Kendall Jenner showed off her quintessential Aspen style with a glamorous long white teddy trench atop an all-black outfit. She finished the look with a festive leather purse covered in silver embellishments. (‘Tis the season!)

Justin and Hailey Bieber tagged along for the evening in their signature head-turning styles. Hailey wore a gargantuan grey shearling coat by Ferragamo with a black fuzzy handbag, leather boots and Matrix-esque shades. For his look, Justin matched his wife’s dark palette in a leather blazer with black loose pants. In true Mr. Bieber style, he threw things off just a touch with the addition of a trucker hat.

Festive and comfortable

A themed holiday sweater never gets old, just ask Kendall Jenner. Before hitting the slopes Aspen style on Sunday, Jenner sported a festive model-off-duty look comprising a patterned winter sweater, cargo ski pants and Ugg boots (a cozy girl must-have).

With her hair pulled into pigtails and her trusty skinny shades on, Jenner looked ready to fly down Aspen’s snowy slopes. More importantly, she successfully got us excited for winter.