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Get the Looks
Hiking and active
- Varley Hawley Half-Zip Sweatshirt
- Alo Yoga 7/8 High-Waist Airbrush Legging
- Alo Yoga Airbrush Real Bra Tank
- Vuori AllTheForm Pocket Legging
- Free People Movement Mountain High Half-Zip Fleece
- HOKA Clifton 11 Sneakers
- Veja Venturi II Sneakers
Walking around town
- Anine Bing Tyler Sweatshirt
- Jenni Kayne Linen Logan Shirt
- Loro Piana Valerio Linen Wide-Leg Pants
- Vince Cashmere Oversize Sweater
Dinner
Wondering what to wear in Aspen in fall? Here is how I spent an easy week in early September: no rushing, no rigid itinerary, just lots of walking, good food and mountain air. Below is the full recap, plus the hiking, town and dinner outfits I would pack for each outing.
Arrival Day: Walking, Tavern Lunch and Ice Cream
Monday, Sept. 7
We got in, dropped our bags and headed straight to White House Tavern for a relaxed first meal. After that we checked out the hotel pool, wandered through town and ended the afternoon with ice cream from Paradise Bakery. We kept dinner light and skipped a late night out.
What to wear: an easy travel-day look that still feels pulled together for a patio lunch.
- Anine Bing Tyler Sweatshirt – a soft, polished layer for cool mountain air. Shop it here
- Loro Piana Valerio Linen Wide-Leg Pants – breezy and elegant for walking all afternoon. Shop it here
- Veja Venturi II Sneakers – comfortable enough for a full day on your feet. Shop it here
Morning Workouts and the Maroon Bells Hike
Tuesday, Sept. 8
We started with a workout in the Technogym at the hotel, then had breakfast at the hotel before heading to the Maroon Bells. It is one of the most beautiful hikes around, so bring a camera. The rest of the afternoon was pool time.
Local tip: mornings are crisp, then it is warm by noon. Layer a half-zip over a tank you can peel off.
- Varley Hawley Half-Zip Sweatshirt – the cozy layer for chilly mornings at altitude. Shop it here
- Alo Yoga 7/8 High-Waist Airbrush Legging – sleek enough for the trail, polished enough for lunch after. Shop it here
- Alo Yoga Airbrush Real Bra Tank – a base layer that feels like nothing. Shop it here
- Veja Venturi II Sneakers – a light, grippy sneaker for easy trails. Shop it here
Dinner at Casa Tua
That night we went to Casa Tua. It was the dressiest night of the trip, but still Aspen dressy: elegant without trying too hard.
What to wear: a breezy linen dress and a flat sandal.
- Majorelle Piera Linen Mini Dress – easy, airy and just dressy enough. Shop it here
- Ancient Greek Sandals Eleftheria Leather Sandals – a classic flat sandal that goes with everything. Shop it here
A 20-Mile Bike Ride on the Rio Grande Trail
Wednesday, Sept. 9
This was our big active day. We rode about 20 miles along the Rio Grande Trail to Woody Creek Tavern, a classic stop. While there, I picked up a hat from the Aspen Hat Lady, and then we rode back. Afterward we sat by the pool, and we finished the day with dinner at Wild Fig.
What to wear: something breathable and comfortable that still photographs well.
- Alo Yoga Airbrush Real Bra Tank – lightweight and breathable for a long ride. Shop it here
- Vuori AllTheForm Pocket Legging – pockets for your phone and a no-fuss fit. Shop it here
- HOKA Clifton 11 Sneakers – cushioned for miles of trail. Shop it here
Shopping, Coffee and Football with Room Service
Thursday, Sept. 10
Thursday was all about wandering. We walked around town and stopped in at Kemo Sabe, then had coffee at Sant Ambroeus. Back at the hotel, we had a glass of champagne and watched the football game with room service. It was a perfect low-key night.
What to wear: a crisp linen top for the town stroll, then something cozy for a night in.
- Jenni Kayne Linen Logan Shirt – polished and easy for shopping and coffee. Shop it here
- Vince Cashmere Oversize Sweater – the cozy layer for champagne and football. Shop it here
Gondola Hike, Mini Golf and U.S. Open Semifinals
Friday, Sept. 11
We began with the Technogym, then grabbed a Morning Glory muffin to take on our hike. Afterward we had lunch at the top of the gondola, and then an iced cappuccino from Paradise Bakery. Later we played mini golf, and back at the hotel we watched the men’s U.S. Open semifinal. We ended the trip with dinner at Meat & Cheese.
What to wear: a hike outfit that transitions easily to mini golf and dinner.
- Free People Movement Mountain High Half-Zip Fleece – a warm layer for the top of the gondola. Shop it here
- Alo Yoga 7/8 High-Waist Airbrush Legging – comfortable from trail to mini golf. Shop it here
- HOKA Clifton 11 Sneakers – cushioned for the downhill. Shop it here
My Aspen Highlights
- Best meal: Paradise Bakery in the morning: a Morning Glory muffin and an iced cappuccino
- Best activity: The Maroon Bells hike
- Favorite find: the hat from the Aspen Hat Lady
- Best low-key night: champagne and football with room service
Final Thoughts on What to Wear in Aspen in Fall
Aspen does not need a packed schedule to feel special. Between the hikes, the bike ride, the pool and all the walking around town, this was the kind of trip that resets you. If you are planning what to wear in Aspen in fall, pack layers, one or two elevated dinner outfits and comfortable shoes, and you are set.
Planning your own trip? Here is my guide to How to Dress for Aspen in Summer, plus more ideas on what to wear in Aspen in fall right here.
