The Fashion-Person Guide to Aspen: The Trendiest Spots to Visit and Be Noticed

      Welcome to Who What Wear Travels, a series of curated guides to the fashion world's favorite destinations. This serves as your source for everything from the most stylish accommodations to unforgettable meals and the ideal travel wardrobe, all reviewed by fashionable locals and well-traveled individuals. From December to mid-March, brands, celebrities, influencers, and ski enthusiasts flock to Aspen. With figures like Kendall Jenner, Hailey Bieber, and Jennifer Lopez frequenting the area, it seems everyone who’s someone heads to Aspen as winter sets in. With the 2025–2026 ski season approaching, it's the ideal moment to assemble our ultimate Who What Wear–endorsed travel guide. Whether you're a repeat Aspen visitor or planning your first trip, consider this your go-to resource for the trendiest places to stay, eat, drink, shop, and enjoy skiing or snowboarding. We consulted two Aspen experts for their inside tips: Shea Marie, CEO and founder of SAME, and Wendy Kunkle, president of the iconic Aspen hat shop Kemo Sabe. From popular celebrity haunts to reliable local favorites, we’ve got the information you need to make your Aspen trip the most stylish yet.

      **When to Visit**

      Aspen truly comes alive during the peak ski season from December to March, making it the best time to experience the area’s famous slopes and vibrant social scene. However, Marie argues that any time is a great time to visit. "Until last year, I had only experienced winter or summer—both equally beautiful and special," she shares. "Recently, I spent several weeks in the past few months, which was my first experience of fall in Aspen, and it might just be Aspen’s best-kept secret. The days are warm while the nights are crisp, crowds are thinner, wildlife is abundant, and the trees are golden. I might go as far as to say it’s my new favorite season." According to Marie, the summer is ideal for hiking, the fall for a relaxing retreat, and winter for top-notch skiing, snowboarding, and people-watching.

      **How to Get There**

      There are two primary routes to Aspen: either fly directly to Aspen Airport (which can be tricky due to winter storm-related cancellations) or arrive in Denver and drive the scenic two to four hours through the mountains. Kunkle mentioned a little-known third option: landing in Grand Junction. "It's about two hours away, and the drive doesn’t include treacherous mountain passes like the route from Denver," she explained. Upon your arrival, Kunkle notes that renting a car isn't necessary. "Aspen is very walkable, with excellent restaurants, shops, and the chairlifts for Aspen Mountain all centrally located."

      **Where to Stay in Aspen**

      **Hotel Jerome, Auberge Collection**

      Described by Kunkle as "a true Aspen landmark," Hotel Jerome first opened its doors in 1889 during Aspen's silver boom. It has welcomed everyone from cowboys to Hunter S. Thompson and is rich with character and history. The ambiance feels both historic and luxurious, as if you’ve entered Ralph Lauren’s private ranch house, imagines Marie. "Plus, it’s home to two of the best bars in town," Kunkle adds. J-Bar, which Marie claims has the best burger around, and the cozy Living Room bar, which is the ultimate spot to see and be seen.

      **St. Regis Aspen**

      The St. Regis has long been a fixture in the town, hosting the Snow Polo every December and home to the famous hotel dog, Kitty Jacob Astor II, a Bernese mountain dog serving as the resort's mascot. During ski season, the Snow Lodge occupies the hotel terrace, featuring trendy brand activations, DJ performances, and winter events.

      **Travel Tip:** Arriving hungry? If it’s before 2 p.m., stop at Louis Swiss Bakery just next to the airport for some of the best pastries and sandwiches in town.

      **Mollie**

      Mollie is the latest luxury hotel to join Aspen's lineup and stands out with its sleek, modern design and an on-site restaurant brought in from L.A. This 68-room boutique hotel opened in December 2023, incorporating contemporary Scandinavian and Japanese designs. Next month, it will debut a new restaurant, Petit Trois, an acclaimed French bistro by Chef Ludo Lefebvre.

      **Additional accommodations to consider:** The Little Nell, the only ski-in/ski-out option at Aspen Mountain with a dedicated ski concierge and what Marie claims is the best hot chocolate in the area. W Aspen is a more recent addition to the town’s growing hotel offerings, bringing its well-known cultural appeal to the base of Aspen Mountain.

      **Where to Dine in Aspen**

      **Caribou Club**

      Established in 1990, Caribou Club is viewed as the most prestigious private members' club in Aspen. With its dimly lit space