One of the world's fabled resorts, Aspen practically defines glitz, glamour, and glorious skiing. To the uninitiated, Aspen and Vail might be synonymous. Between the galleries, museums, music festivals, and other glittering social events, there's so much going on in Aspen that even in winter many people come simply to "do the scene," and never make it to the slopes. High-end boutiques have been known to serve free cocktails après ski.
At the same time, Aspen is a place where some people live average lives, sending their children to school and working at jobs that may or may not have to do with skiing. It is, arguably, America's original ski-bum destination, a fact that continues to give the town's character an underlying layer of humor and texture. You can come to Aspen and have a reasonably straightforward, enjoyable ski vacation, because once you've stripped away the preciousness, Aspen is simply a great place to ski.
Aspen has always been a magnet for cultural and countercultural types. The late bad-boy gonzo journalist Hunter S. Thompson was one of the more visible citizens of the nearby community of Woody Creek. One of Aspen's most amusing figures is Jon Barnes, who tools around in his "Ultimate Taxi" (it's plastered with rainbow glasses, crystal disco balls, and neon necklaces, and is redolent of dry ice and incense). You'll find everyone from socialites with Vogue exteriors to long-haired musicians in combat boots and fatigues. Ultimately, it doesn't matter what you wear here, as long as you wear it with conviction.