1. The Trucker Hat
While passé to some, this style of cap has proven eternal from Smuggler Trail to the deck at Cloud Nine. Venerable nonprofit organizations proudly emblazon their initials across their oversize crowns (AVSC, ACES, etc.). Eskyflavor hats are particularly loud with cheeky phrases such as “POW” or a bejeweled “Snow Bunny,” as are Aviator Nation’s “Pray for Surf” mantra hats. Aviator Nation hats from $45, 308 S. Mill St.
2. The Suede Jacket
At 8,000 feet above sea level, even in summer, the temperature cools off at night. A suede jacket takes you from cocktails to dinner in comfort. It’s not as formal as a blazer and not as casual as a down puffer. Like Aspen, it has Western roots and its supple fabric only gets better with age. 520 E. Cooper Ave., pitkincountydrygoods.com
3. The Leggings
The female of the Aspenite species is never long without her favorite pair of leggings. She wears them on hikes, to Pure Barre, to the café. Lululemon, or mecca to some, continues to advance form-fitting technology. Outdoor Voices popped up in 2017; ever since, its tonal colorblocked staples have been seen on gams around town. Lululemon leggings from $98, 204 S. Galena St.; Outdoor Voices leggings from $70, 625 E. Hyman Ave.
4. The Ski Jacket
A good ski jacket is nonnegotiable. The most under-the-radar brand is Authier, an Italian-based heritage line designed in collaboration with local shop owner Lee Keating, of Performance Ski. The store is also the town's exclusive retailer of Aztech Mountain, coats designed specifically for men by Aspenite Heifara Rutgers. From $1,250, 614 E. Durant Ave.
5. The Trail Running Shoe
The iconic footwear of Aspen must be a pair of Salomon Speedcross. They’re a hybrid: the low profile and flexibility of a sneaker mixed with the tread of a hiking boot. The shoes handle uphill, downhill and icy sidewalks with ease. From $140, 210 S. Galena St., utemountaineer.com