Aspen Long Weekend: Where to Go & What to Wear

Aspen Long Weekend: Where to Go & What to Wear

I had the pleasure of traveling to Aspen over Presidents Day weekend this year for a special dinner with Rebecca Minkoff at Snow Lodge on the 17th of February. Here’s my experience and some simple tips for a successful Aspen weekend!

It was my second time going to Aspen so I knew in advance it could be a bit tricky flying in and out of ASE airport.

I always like to wear my most comfortable leggings as well as something that looks smart layered to the airport in case I get hot or cold on the plane. Likewise, I try to avoid checking a bag and tend to arrive a little earlier to the gate. This is especially important for trips flying with stops into Aspen; my friend arrived very late to the gate and was forced to check her bag which United eventually lost for over 24 hours…

As it happens, the last leg of my flight from Denver to Aspen was canceled, leaving me stranded without any alternatives offered by the airline (United). Fortunately, after about six Ubers cancelled we found one that was willing to go for a 5 hour drive – and back again – in the snow storm! Thank goodness, otherwise we would have missed the entire weekend! After a very long trip we eventually arrived in Aspen.

The following day was beautiful and clear, as was the rest of the weekend. I was struck by the serene and silent beauty of the mountains. I love snow because it acts as a natural noise dampener and makes everything seem more peaceful. Downtown Aspen is small but lively during the busy seasons.

During the day of the 17th we went shopping downtown. There are a lot of cute boutiques and even some cool second-hand stores. I got a beautiful and light silk Haute Hippie skirt for summertime at the thrift store as well as a nice button down top to match my Rebecca Minkoff pants for the dinner in the evening. During this first day shopping I wore my large black jacket, some trendy high waisted boot cut leggings and a zip-up black wool cardigan. The style in Aspen, generally speaking, is casual glam. I could have been a bit more flashy; I was still thinking like a New Yorker.

The special VIP dinner in the evening at Snow Lodge in the St Regis hotel was fantastic. It was in honor of the Rebecca Minkoff pop-up at the St Regis as well as her latest NFT drop. Paris Jackson gave an intimate performance during the end of dinner.

I wore my Rebecca Minkoff pants, sweater and purse as well as the animal print inspired button down shirt that I’d bought in town. I paired this with silver stilettos and gold jewelry.

I met some very interesting people at the dinner, including former Olympic sprinter, Ella Nelson.

After dinner we went to the “Red Room” which had amazing art and was ironically quieter than the restaurant. I pretended to DJ.

Beware that you may have to walk back to your hotel because there aren’t any Ubers or Lyfts in Aspen. Many people wear nice boots instead of heels. However, Aspen does have an old fashioned taxi service – but with limited drivers. There’s also an app called “Downtowner” that gives you a free ride from many popular locations within the small downtown area. It ends at 11pm and doesn’t service the airport nor the ski slopes. However, the bus system works very well to get to the mountains and is also free. The logistics can be a bit stressful if you don’t know!

After the amazing Rebecca Minkoff dinner my friend and I decided to go skiing the next day! We needed a few items such as gloves etc so we went to shop at Replay (a second hand ski gear boutique). I skied quite a lot as a child and later lost my enjoyment, but I feel like this trip I got it back! I had such a fun time just going for a short little bit to a familiar mountain.

The trick is to keep your legs parallel and to always bend your knees. My fashion tip for skiing? Go bold! Bright pink or yellow one pieces make a statement. If you want a two piece, make sure you wear a bright hue that flatters your coloring. That’s why I love this blue jacket. Also, never forget sunglasses!! Otherwise, you could literally damage your retina and get snow blindness in certain scenarios. Snow is very reflective, you’ll want to bring your sunglasses around town with you as well, just for your comfort.

Après-ski is a big deal in Aspen! It’s the time to let loose and relax or let off some steam. Basically, it’s happy hour with more style and winter gear. It’s not my personal taste, but people in Aspen tend to sport a lot of obvious labels. If that’s your thing, bring it on out!

We did a post-ski hot tub dip at our lovely hotel, Hearthstone House. The hot water felt so good contrasted against the cold air outside. So don’t forget your bikini! I opted for something classic but you can get away with glitz here if you want. So go for it!

Then we got in our robes for a few minutes of “wine and cheese hour” at our bed and breakfast, Hearthstone House.

I would highly recommend this spot as a good option to book as they also had daily breakfasts and all-day tea included with the room. It was also very local to everything downtown.

In the evening we had a lovely dinner at Snow Lodge in the St Regis again. It was the best risotto I’ve ever had!

The Paloma cocktail was also so fresh and delicious. I wore a simple knit black dress with a red Natural Nuance bag and boots. I also brought a black faux fur vest just in case. Many people were wearing designer sweaters and elevated trousers as well.

It’s a very lively restaurant as you can see! They have an area upfront for a DJ and dancing so you definitely won’t be bored. After dinner, we made our way to the Red Room again then  we left the St Regis and headed towards the Caribou Club.

It was only a couple blocks walk; Aspen is very small.

At the club I ran into acquaintances from New York and also spoke with a few interesting people from LA. It was
roughly an equal mix of couples and singles, which is definitely different from the clubs in New York City. They also have a charity game of blackjack which I had fun playing for a few minutes.

I left after a couple hours while my friend stayed late into the night. If you wear something cute in the day, you don’t have to worry about changing for the club.



On Saturday I attended a Bob Moses concert in the courtyard of the St Regis. What a delight! There were various yurts set up, including the Rebecca Minkoff pop-up.

It was quite chilly so I wore my black sparkly Levi’s with my boots and my blue ski jacket. As cold as it was, it was so lovely to be outside with the mountains during the concert. What a view!

We then enjoyed some more risotto (really good!!) in the red room with some drinks too. They also have the BEST pistachio gelato. So good! Aspen is at 8000ft elevation so alcohol will effect you more strongly – be careful. We couldn’t finish the bottle!

Sadly, we had to fly back the following day in advance of the storm coming in on Monday. There was a bit of an issue booking a taxi last minute, so I would advise you to do it the day before.

As much fun as I had, I was glad to get back to NYC and the people here I miss. As they say, there’s no place like home!

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Comments: 2

  1. future100100 says:

    wow wow wow wow wow wow wow wow!!!

  2. future100100 says:

    Amazing, you are so impressive! Your trip looks really fun and star lit! You are a super star super model!

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