The first time I visited Aspen was in the summer. The rolling mountains look just as beautiful in the warmer months as they do when they’re capped with snow, but what’s even better than the resort town views? The impeccable style.
If you’re looking for ways to get through a winter outfit slump, the streets of Aspen are a smart place to start. You’ll find ensembles that go beyond just carrying the latest It bag or wearing a trendy label. It’s a thrilling mix of layered textures, unexpected yet wearable styling techniques, and updated silhouettes set to dominate 2026.
Of course, there’s the usual circuit of celebrities who visit the city annually—you know, the Kardashians and Hadids of the world. That said, there are also a slew of under-the-radar tastemakers putting the ski destination on the sartorial map.
See how they’re mastering the art of cold-weather dressing ahead.
Go a Little Wild
If your black-and-white outfits are feeling a bit monotonous, add a splash of leopard, à la Bella Hadid, with a printed handbag. Hadid’s vintage Fendi proves the animal print is a forever staple—and there are plenty of current options to shop, including the coveted Saint Laurent vanity pouch, below.
Return to Retro
Take a trip back in time with a vintage-inspired coat. Helsa’s dramatic rendition is at the top of several wishlists because it’s an outfit maker in its own right, but also serves when worn pared back with joggers. Click the link for proof.
Lovers and Friends Elias Hat
Helsa The Irina Faux Fur Coat
Quay Australia Aura Points
Relaxed to the Max Trousers
The shift away from ultra-baggy to tailored-relaxed pants continues. You’ll earn bonus points for testing out a pair in the color of the moment: rich hot chocolate. And if you want your legs to feel like they are being hugged, slip on a pair of cozy long johns underneath.
Staud Betsy Cashmere Sweater
The Garment Damiy Faux Fur Long Jacket
Staud St. Regis Harlow Bag
Fringe Benefits
Textured treasures make winter dressing fun. From the tassels on this suede jacket to the studs on this crossbody bag, this is one of the chicest ways to make everyday cold-weather outfits pop.
Re/Done Suede Fringe Jacket
Madewell The Perfect Vintage Wide-Leg Jean
Prada Brown Leather Crossbody Bag
Now 34% Off
Reformation Caludette Bootie
Wrapped Wonder
The elongated silhouette of a maxi cardigan feels both grounded and elegant during chilly months. To keep the look from overwhelming your frame, pair it with a hat to draw the eye upward. Lastly, add leather gloves for a look that feels alpine and artisanal while nodding to time-honored weaving motifs.
8 Other Reasons Belis Rancher Cowboy Hat
W.J.W. Aspen Aprés-Ski Look
Polo Ralph Lauren Mini Polo ID Leather Shoulder Bag
Nordstrom Dauphine Kitten Heel Knee High Boot
Now 55% Off
Cream of the Crop
From fall’s cropped trench coats to winter’s short shearling jackets, hems that hit right at the waist make your favorite pair of jeans feel new again. Have fun with a fluffy design and pair it with an unexpected white handbag.
River Island Trophy Jacket
Now 49% Off
Still Here Everyday Relaxed Mid-Rise Jeans
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