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 ultimateBest Knockoff Luxury Clothing 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
Hotel Jerome, Auberge Collection
"A true Aspen landmark," says Kunkle of the Hotel Jerome. First opened in 1889 during the height of Aspen's silver boom, the Jerome has opened its doors to everyone from pre ski resort cowboys passing through town to Hunter S. Thompson and is brimming with the character and history to prove it. The aesthetic feels historic yet luxurious, like maybe you’ve stepped into Ralph Lauren’s private ranch house, Marie imagines. "Plus, it’s home to two of the best bars in town," Kunkle adds. J-Bar, which Marie says has the best burger in town, and the cozy Living Room bar and lounge, which is the ultimate place to see and be seen in town.
The St. Regis Aspen has long been a cornerstone of town. It's the site of the Snow Polo each December and home to Aspen's most famous four-legged friend, the official hotel dog, Kitty Jacob Astor II, a Bernese mountain dog who serves as a mascot and ambassador for the resort. (Do yourself a favor and follow the TikTok page.) Then there's the Snow Lodge, which descends on the hotel terrace during ski season, bringing a roster of buzzy brand activations, DJ sets, and events throughout the winter season.
WWW Travels tip: Hungry when you land? If it’s before 2 p.m., stop at Louis Swiss Bakery. It’s right next to the airport and has some of the best pastries and sandwiches in town.
Mollie is the newest addition to Aspen's luxury hotel lineup and is already punching above its weight with a sleek, modern design aesthetic and on-site restaurant imported from L.A. The 68-room boutique spot opened its doors in December 2023 with a blend of contemporary Scandinavian and Japanese designs. Next month, it will add a new restaurant, Petit Trois, Los Angeles's acclaimed French bistro from Chef Ludo Lefebvre.
More stays to jot down:
- The Little Nell is the only ski in, ski out option on Aspen Mountain and has a private ski concierge and what Marie says is the best hot chocolate in town.
- W Aspen is a newer arrival to the town's growing hotel scene and brings its notorious cultural cache to the base of Aspen Mountain.
Where to Dine in Aspen
An Aspen institution since 1990, Caribou Club is considered the most prestigious private members' club in town. The space is dimly lit with dark wood paneling and tartan carpeting—stepping inside is like uncovering a relic of a past era. It's part restaurant-bar, part nightclub, part catering business, and spotting a famous face isn't just likely—it's almost guaranteed. "If there is a bold name, whether celebrity or business, they have been in the club," the website states.
Part Northern Italian restaurant, part members' only club, Casa Tua is one of Aspen's best places to see and be seen while twirling your fork around a plate of cacio e pepe. "All of Casa Tua is great, but the upstairs members club is my favorite place to dine in Aspen," says Marie. "It’s cozy with a fireplace, it has an 'everyone knows everyone' feeling, and looks like you’re dining at a beautiful private chalet."
Betula is the perfect balance of Aspen's glitz and glamour and its classic, cozy side. Make your way up to the second-floor space and slip into one of the cloud sofa like booths, and you'll immediately feel right at home, even if home is really thousands of miles away.
More restaurants and cafés to jot down:
- Clark’s Oyster Bar
- Matsuhisa
- Pine Creek Cookhouse
- Sant Ambroeus
- Bonnie's
Where to Après-Ski in Aspen
The team behind the Surf Lodge, Montauk's viral live-music venue, have made their way out West with the arrival of the Snow Lodge. It boasts an impressive lineup of top DJ sets on an outdoor stage at the St. Regis. "It's the number one place for après-ski fun," says Marie. "Everyone is bundled up in their warmest looks—ear muffs, mittens, and all—as the sets are outdoors, snow or shine. You have to try the hot toddy in a mug."
WWW Travels tip: One drink at altitude = three drinks at sea level, Marie warns. Don't forget this on your nights out!
There's no better feeling than coming off the mountain after your last ski run of the day and immediately ordering a round of drinks. If you came to Aspen to ski, then look no further to Ajax Tavern for a prime location at the base of Aspen Mountain and even better people-watching. "It's the perfect spot to sit outside with a Cowboy Coffee and take in the scene," says Kunkle. And if you're stopping in for lunch, I'd add that the grilled cheese and tomato soup is a must.
Despite its small-town feel, Aspen has no shortage of nightlife, and Belly Up is one of the live-music mainstays since 1974 where you might just catch a show—everyone from Willie Nelson to Khruangbin.
WWW Travels tip: Check the Aspen Chamber for current events, Kunkle says, as there’s always something fun happening in town.
More après-ski spots to jot down:
- Cloud Nine Alpine Bistro is famous for its European-style on-mountain parties.
- The wine bar at The Little Nell is a favorite ski in, ski out spot at the base of Ajax.
- J-Bar at the Hotel Jerome is a favorite among locals and in-the-know visitors alike.
Where to Ski and Snowboard in Aspen
"For location, convenience, and ease, [Aspen Mountain] can’t be beat," Marie insists. The chairlift is right in town, making it Aspen's most accessible resort. Even if you're not skiing, take a gondola ride up to the chalet for lunch with a sweeping view. The terrain here is notoriously challenging, however, and Marie warns that it’s not a great mountain for beginners, as there are no green runs.
WWW Travels tip: Drink a ton of water! Aspen is at a high altitude of almost 10K feet (much higher than European ski destinations, etc.), and altitude sickness is a real thing. I always refrain from alcohol for the first 24 hours and drink as much water as possible.
"As a snowboarder, I love Snowmass," Marie says. "The obvious con is that it’s a 20-minute drive from town, but if you don’t mind the drive, it offers so much more terrain—about five times more than Ajax [Aspen Mountain]. You can spend a whole day at Snowmass and not have to do the same run, which is impossible at other resorts. Also, the wide-open long runs are very snowboard-friendly."
Aspen area's terrain is largely considered expert-level, but Buttermilk is the exception. "It’s perfect for non-expert snowboarders," Kunkle says. "The trails are easy to navigate, and if you get there early, the parking is unbeatable. After a day on the slopes, I always head to Home Team BBQ—the food is hearty, warm, and exactly what you want after being out in the cold."
More Aspen activities to jot down:
- Aspen Highlands is the fourth ski resort in the area and favored for its back bowls and expert-level terrain.
- Pilates classes at High Terrain and O2.
- Hiking Smuggler Mountain Trail—it's the perfect quick fix with rewarding views at the top.
Where to Shop in Aspen
You can't go shopping in Aspen without going to Kemo Sabe. I don't make the rules. Having a custom cowboy hat made at the brand's original boutique is probably the most "Aspen" shopping experience you can have. Beloved by droves of celebs including Rihanna and J.Lo, the store is "laid-back luxury meets the Wild West," says Marie, who also points out that they even have a private bar upstairs you can rent out. It's truly a one-of-a-kind experience.
So much of the style and design here references Ralph Lauren's iconic Western-luxe aesthetic, so it comes as no surprise that the Aspen outpost is an immersive shopping experience. Kunkle says it's long been her go-to for timeless Western style and that the team always finds exactly what you need "or, more often, what you didn’t know you wanted!"
WWW Travels tip: You don’t need to reserve a car. Aspen is very walkable, and a reliable bus system makes it easy to get to other nearby mountains.
Although the shopping options in Aspen skew designer—Prada, Gucci, and Balenciaga all have ski-focused boutiques in town—it's still home to local retailers like Pitkin County Dry Goods, where local brands like Pointed Arrow jewelry and Archer Cashmere mingle with labels like Proenza Schouler and Isabel Marant. "The buyers are always on point," Kunkle boasts.
More Aspen shopping to jot down:
- Radio Boardshop is Kunkle and her family's go-to for snowboarding needs.
- Prada is a fashion person's skiwear dream come true.
- The Revolve and Fwrd pop-up shop brings the e-tailers' worlds to life IRL.
What to Pack for Aspen
As much as Aspen is a ski resort town at its core, let's face it: It's also far more stylish than what the average. The mood is elevated and chic but still practical. Think fluffy faux-fur outerwear, sleek riding boots, and a few Western touches through a belt or Stetson-style hat. "Aspen isn’t as dressy as people think: Athletic wear rules the day, and anything goes at night," Marie notes, but says to avoid high heels due to the cobblestone streets and instead wear cowboy boots. "And, of course, top it off with a Kemo Sabe hat—perfect for rain, snow, or shine," she adds.
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