Why is Aspen so cool?
- 2 days ago
- 3 min read
Let's settle something right now. Aspen is not cool because of the skiing.
The skiing is excellent, of course. Four mountains, legendary powder, spectacular terrain. Wonderful. Congratulations, you have arrived. Strap on a pair and head for the back bowls.
But there are plenty of places with great skiing. Utah has snow. Montana has snow. Vail has snow, hell, even Vermont (eweee) has snow.
What those places don't have is a billionaire in Brunello Cucinelli standing next to a guy in a twenty-year-old ranch jacket holding $40 tequila cocktails at the Saturday Farmers market.
That only happens in Aspen.
Aspen is cool because it remains gloriously, unapologetically Aspen.
It is one of the few places left in America where wealth isn't hidden, success isn't apologized for, and nobody feels compelled to pretend that a Gulfstream is somehow less desirable than a bicycle. Oh, and a recent look at the Pitkin County Airport apron showed no less than 40 private jets, some with sticker prices above $50M.
This is a town where hedge fund managers, Hollywood stars, cowboys, tech founders, socialites, Olympians, and ski bums somehow coexist in perfect harmony. The people watching alone deserves its own admission fee.
At breakfast, you'll spot a celebrity desperately trying not to be recognized while wearing a baseball cap, sunglasses, and approximately $12,000 worth of "casual" clothing. By lunch, you'll see a family whose outerwear budget could comfortably finance a small Midwestern college.
If you are a watch spotter, walk right by the Submariners and Datejusts and focus more on the F.P. Journe’s, Mille’s and A.P. Skeletons. It’s a wrist enthusiasts’ runway.
And somehow, nobody seems particularly impressed. Because that's Aspen's secret.
Then there is the fashion.
Aspen has become the unofficial capital of luxury mountain style. Cashmere, shearling, vintage denim, cowboy boots, Shirts with just the right wear and tear and enough stealth wealth to make Milan nervous. One minute you're walking past someone dressed head to toe in Ralph Lauren Purple Label, the next you're standing behind a rancher who owns 5,000 acres and still drives a fifteen-year-old pickup with Beau the black lab in the back.
Both look entirely appropriate.
Any discussion of Aspen would be incomplete without tipping a hat to the town's most over the top, and oddly irresistible, institution: Kemo Sabe.
Officially, it's a western wear store. It’s part retail, part nightclub, part social experiment. You walk in intending to "just look around" and forty-five minutes later you're ordering a custom hat, branding your initials into the brim, and wondering whether you really need a pair of exotic boots that cost more than your first car and laying out the Amex for +$5K.
No bother boxing them up…put them on and head upstairs to one of their legendary parties.
Wendy Kunkle, Kemo Sabe’s gregarious Owner/Proprietor and Host, has crafted a private VIP bar above the Kemo Sabe sales floor, making it one of Aspen's most coveted invitations, hosting everyone from celebrities to billionaires, wedding parties, and the sort of people who casually refer to "the jet" as though everyone has one. Cocktails flow, country music blares, custom hats are commissioned at prices only tolerated if inebriated and pretty soon there are complete strangers dancing together wearing matching cowboy hats they purchased three hours earlier. It is wonderfully absurd and quintessentially Aspen.
And while, winter may make the headlines, Summer may be Aspen's greatest trick, because summer is when Aspen gets the locals to come into town.
Morning coffee runs will be in the low 40’s but there are always 75 degree afternoons. No humidity. Fly fishing. Polo. Hiking. Outdoor concerts. Farmers markets. Patio lunches at Casa Tua or Hotel Jerome and plenty of people watching.
Of course, Aspen is expensive. Spectacularly, irrationally, occasionally hilariously expensive. Hotel rooms can induce heart palpitations. A casual shopping trip can quickly resemble a down payment on a house. All of the brands are there: Ralph Lauren, Moncler, Gucci, Louis Vuitton, Prada, Dior, Zegna, Rolex, Chanel, Fendi…the list never ends. Only in Aspen can you buy a $6,000 cashmere sweater, a $50,000 watch, and a custom beaver felt cowboy hat before lunch, all without moving your car.
And around it all, Aspen delivers something increasingly rare in luxury travel: authenticity.
It remains a place where success is celebrated, style matters, nature dominates, cocktails begin early, and life is meant to be lived in person, not through a screen. Aspen somehow still feels real.
Granted, it is very, very expensive reality.
But reality, nonetheless.
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