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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.
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For the hotel nights, decant your usual shampoo and body wash into refillable travel bottles before packing. Keep these small essentials in the toiletry bag so the rest of the suitcase is for the layers and dinner pieces.
Day One: Arrival, White House Tavern and Paradise Bakery
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.
Photo credit: Veja
Photo credit: Anine Bing
What to wear for White House Tavern and the town walk
Keep the arrival outfit relaxed for lunch and the stop at Paradise Bakery: your grey sweatshirt, straight jeans and a town sneaker. The New Balance women’s 327 sneakers are another town-shoe option with straight jeans and a sweatshirt. Keep trail footwear for the hikes rather than treating these as a substitute.
- The black Jenni Kayne Linen Logan Shirt is the current color option for a loose linen layer with straight jeans. Wear it beneath your own grey sweatshirt when the air cools.
- Veja Venturi II Sneakers – comfortable enough for a full day on your feet.
Photo credit: Madewell
Day Two: Morning Workout and the Maroon Bells
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. Trail shoes with real grip are worth packing for it: the Salomon X Ultra 5 Low GORE-TEX hiking shoes are light, waterproof and made for routes like this. The rest of the afternoon was pool time.
Photo credit: Barbour
Local tip: mornings are crisp, then it is warm by noon. Layer a half-zip over a tank you can peel off.
- ANINE BING Harry Shrunken Signet Sweatshirt in ecru – a soft fleece layer for the morning warm-up. Keep a separate weather-ready layer for the hike.
- Alo Yoga 7/8 High-Waist Airbrush Legging – sleek enough for the trail, polished enough for lunch after.
- Alo Yoga Airbrush Real Bra Tank – a base layer that feels like nothing.
- Veja Venturi II Sneakers – a town sneaker; choose trail footwear suited to your hike instead.
Photo credit: Hunter
What to wear: Maroon Bells trail conditions
Use trail footwear suited to the route and conditions, not a town sneaker by default. Try your socks and shoes together before the trip; add a weather layer and the water and safety kit for your chosen walk.
For the trail, pack women’s merino-wool hiking socks. Try the socks inside your trail shoes before the trip and choose the height, cushioning and size for your walk.
Photo credit: FP Movement
Day Two Evening: 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. The black Tibi sleeveless knit dress below is the packing option for this dinner. For a daytime layer, see the Tibi Feather Weight cashmere crewneck in ivy green.
What to wear at Casa Tua: black Tibi sleeveless knit dress
For dinner at Casa Tua, the black Tibi Compact Ultra Stretch Knit Sleeveless Dress keeps the line clean without ball-gown volume. Wear it alone with a small evening bag, or over a fine knit for a cooler evening. The brand styles it with a belt and boots; those accessories are separate. Add your own warm coat for the walk.
See the black Tibi sleeveless knit dress.
Day Three: Rio Grande Trail, Woody Creek Tavern and Wild Fig
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.
Photo credit: Staud
Photo credit: HOKA
What to wear on the Rio Grande Trail ride
A light tank and pocket leggings work for the ride to Woody Creek Tavern. Choose shoes that suit your pedals, then change for Wild Fig.
- Alo Yoga Airbrush Real Bra Tank – lightweight and breathable for a long ride.
- Vuori AllTheForm Pocket Legging – pockets for your phone and a no-fuss fit.
- HOKA Clifton 11 Sneakers – an option for casual walking; choose footwear that works with your bike pedals and route.
What to wear at Wild Fig: brown Reformation Maven midi dress
Change out of the bike kit for Wild Fig. The brown Reformation Maven midi dress in Mole has a mock neck, fitted bodice and flowing drop-waist skirt. The lined viscose georgette brings a softer evening shape beside sleek boots and a small bag. Carry your own cashmere layer and warm coat for the walk. Sizes are limited, so confirm yours before ordering.
See the brown Reformation Maven midi dress.
Day Four: Kemo Sabe, Sant Ambroeus and a Night In
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.
Photo credit: REI
What to wear for Kemo Sabe, coffee and room service
Wear the cashmere layer with straight jeans for town, then keep it on for champagne and football by the fireplace.
- off-white Vince Plush Cashmere Crew Neck Sweater – the cozy layer for champagne and football.
A black Madewell leather belt with a gold-tone buckle finishes the jeans-and-sweater town outfit.
What to wear: a wet town day
A rainy day needs a different packing plan from a sunny afternoon. Add a waxed jacket and rain boots for damp walks around town.
Barbour Reighton Spey Waxed Jacket
The black Barbour Reighton waxed-cotton jacket is the current color option for damp walks around town. The jacket in the photo is sold out; the link is for black, with sizes 12 and 14 available when checked. Leave room for a sweater underneath and follow the waxed-cotton care instructions.
Hunter Original Tall Rain Boots
Tall black rain boots are an option for wet walks around town. They are rain boots, not hiking boots, and I would keep them separate from the shoes you choose for a mountain trail. black Hunter tall rain boots.
Day Five: Gondola Hike, Mini Golf and Meat & Cheese
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.
Photo credit: REI
What to wear for the gondola and mini golf
Pack a fleece or a packable Patagonia Down Sweater Vest in black for the top of the gondola and trail shoes suited to the route. Change into the dinner dress below for Meat & Cheese.
- Free People Movement Mountain High Half-Zip Fleece – a warm layer for the top of the gondola.
- Alo Yoga 7/8 High-Waist Airbrush Legging – comfortable from trail to mini golf.
- HOKA Clifton 11 Sneakers – a town sneaker; use trail footwear suited to the downhill route.
What to wear at Meat & Cheese: Earth Lilac Staud Effie dress
For Meat & Cheese, the Earth Lilac Effie is the more playful dinner choice, with a draped dark-brown bodice and lilac beaded movement at the skirt. Let the dress do the work: simple boots or heels, a small bag and a coat, without extra statement jewelry. It is a dressier option for the last dinner of the trip.
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 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, or plan colder weather with the Aspen winter guide.
