The Fashion-Person Guide to Aspen: The Coolest Places to Be and Be Seen
Welcome to Who What Wear Travels, a series of curated guides to destinations the fashion set loves. Consider this your download on everything from the chicest stays to the most memorable meals to the perfect travel wardrobe, all vetted by stylish locals and well-traveled fashion folks.
Starting in December through mid-March, brands, celebrities, influencers, and ski fanatics alike all descend on Aspen. Kendall Jenner, Hailey Bieber, Jennifer Lopez—lately it feels like anyone who's anyone is heading there as soon as winter arrives. So now that we're gearing up for the 2025–2026 ski season, it's the perfect time to curate our ultimate Who What Wear–approved travel guide.
Whether you're a seasoned Aspen visitor or are putting together your inaugural trip, let this serve as your North Star for all the chicest places to stay, dine, sip, shop, and ski and snowboard. From buzzy celebrity-beloved spots to tried-and-true local favorites, we have the insider intel on everything you need to know for your most stylish Aspen trip to date.
When to Visit
Aspen largely comes to life during peak ski season from December through March, which is the best time to visit if you're after Aspen's renowned slopes and its buzzy social scene. But Marie insists that there's no wrong time to visit. "Until this past year, I had only spent time in the winter or summer—both equally as special and stunning," she shares. "Recently, though, I spent several weeks over the past few months, which was my first intro to fall in Aspen and dare I say Aspen's best-kept secret. It’s still warm during the day but crisp at night, the crowds have died down, the wildlife is everywhere, and the trees are golden. I might go as far as to say it’s my new favorite season." Per Marie's advice, go in the summer for hiking, in the fall for a calm and cozy escape, and in the winter for peak skiing, snowboarding, and people-watching.
How to Get There
There are two main ways to get to Aspen: flying directly into Aspen Airport (often a challenge as it's notorious for flight cancellations due to winter storms) or land in Denver and make the mountainous two- to four-hour drive along. There is a secret third way, however, which Kunkle divulged: flying into Grand Junction. "It’s only about two hours away, and the drive doesn’t involve any mountain passes, unlike the often treacherous route from Denver," she explained.
As for when you do arrive in town, Kunkle insists you don't need to rent a car. "Aspen is very walkable with all the best restaurants, shopping, board shops, and even chairlifts onto Aspen Mountain all situated right in the heart of town."
Where to Stay in Aspen
