Epic family summer trip recount time.
We spent over a week in gorgeous Colorado this summer with my mom, stepdad, brothers, sisters-in-law and all the kiddos. I don’t know if you’ve ever been to the Rocky Mountains in the summer, but it’s my favorite time to go. Growing up in the South did not afford me the ability to become a skier (neither did my propensity for altitude sickness) but gahhh…get me to the mountains in the summer months and I’m a happy gal.
Aspen Outfit Guide: What I Wore On Our Family Trip
My family feels the same way and has been planning this trip for a couple of years. We went years ago when the kids were tiny and wanted to go back, so a Colorado family trip was on the books! Packing for a place like Aspen in summer can be a little tricky, but I knew we’d mostly be hanging at the Airbnb, doing outdoor activities and only spending a little time in the (fancy) town, so I came to my senses and I chilled for a bit, knowing I can do sporty-casual pretty easily.
I only really brought a couple of dress options for the occasional dinner out and brought, in my true style, plenty of comfy pants, sporty-casual shoes, and fun accessories to make everything feel a little special and not too basic. Keep scrolling for my entire Aspen outfit guide.
1 | Travel Day + Concert Day
Tee (M) | Shirt (M) | Cargo Pants (M) | Sneakers | Carry-on | Mini Roller Bag
We had an early, quick flight over to Denver, a (not-so-) quick rental car pickup, then met up with one of my brothers and his family for a perfectly timed Dr. Dog show at Red Rocks Amphitheater our first night.
We couldn’t believe our luck that they were playing right before our family vacay. So rad! Red Rocks is a simply stunning place to see a show if you’ve never been. Make it happen. (You might even spot a random celebrity like my brother did…they sat behind McLovin for the whole show LOL.)
2 | Second Travel Day, Car Version
The next day we drove the three hours up to Aspen, stopping in lovely Glenwood Springs for lunch. I wore this exact outfit and it was sooo comfy for a car ride. Because it’s been summer, I just wear a swimsuit top with this dress so I don’t have to worry about a strapless, etc.
You can’t really see them here but I love the pale pink Birkenstocks with the bright blue and yellow. Fav combo right now are brights and muted pastels.
3 | Riding The Gondola Up Aspen Mountain For Lunch
Tee (1) | Sweater (M) | Pants (M) | Birks | Bag
After having a fun first night together as a fam, we headed to downtown Aspen the following day to catch the gondola up Aspen Mountain. It’s a blast and the views are absolutely incredible…on par with the Swiss Alps, honestly. It’s a perfect family-friendly activity and you can grab lunch, pictures and some playtime at the top.
It’s spread out enough though that you don’t feel cramped and can roam around and find spots to chill. For some non-kid time, they even offer mountain top yoga in the mornings. If we had been staying in town instead of up on Buttermilk I would have totally made it to one of those.
A sweater, tee and breezy linen pants were perfect for this visit. It can get quite cool at the top in the shade, so it was nice to have that extra light layer.
3 | Horseback Riding Through The Aspen Groves
Hat | Similar Muscle Tee | Cargo Pants (M) | Denim Shirt (M) | Bag
A couple of days later we had a gorgeous trail ride booked at a ranch up near Maroon Bells. We rode through the aspen trees and it was so much fun. I had a sweet mule named Bruce who I’m now a huge fan of and he approved of my comfy outfit for the ride. Long pants and closed-toed shoes are necessary and the denim shirt and bandana, well, felt festive for the occasion. It also added a little pop of color which I’ve become more of a fan of lately.
The littles got to do a pony ride after, too, near a pretty stream. It’s all just as picturesque as you’d imagine in this whole area. Highly recommend a trail ride if you visit the area! My brother took this pic and was laughing at me — hence my funny awkward look lol.
4 | Parent’s Night Out With My Bros + SILs
Tank (M) | Skirt (M) | Sweater (M) | Sandals | Bag
My mom and stepdad babysat and let the parents have a fun night out in downtown Aspen. We had apps at a place appropriately called Meat + Cheese and shopped around a bit before dinner at a rooftop Mexican place called Las Montañas that was so good. If you go be sure to make a rez for the patio if you don’t have a big group.
This little linen blend tank and skirt set from Gap has been a great go-to that feels like a dress but is even easier to wear and mix and match. These Everlane Crossover sandals go on most trips with me since they pack so flat and yet are super comfy for shorter exploring jaunts.
5 | Hiking In Snowmass + The Grottos
Tee (M) | Similar Shorts (M) | Bag | Sneakers
Hiking is a definite must in this area. Our first was a trip just up the road to Snowmass where we did a hike called Ditch Trail. It was seriously beautiful and you could decide how far you wanted to go. This was great for a large group with various ages and really provided some stunning views.
Vuori joggers and shorts go with me on pretty much every trip, whether I wear them for activities or to sleep in. These shorts are also great under skirts or dresses if I need to use them that way. Mine are an older style, but their Daily Biker Shorts look similar and I love their Daily Leggings.
6 | To The Snowmass Rodeo
Hat | Similar Vest | Bandana | Pants (M) | Nikes
Since I didn’t grab an outfit pic (having too much fun) here’s a widget with what I wore.
On one of the most gorgeous evenings there, we headed to the famous Snowmass Rodeo. It was such a blast with a bbq dinner to start with and then lots of fun events to follow. My favorite was the barrel racing which Pinky’s mom used to do in Central Oregon, too! It was awesome to let our kiddo see in person what her grandma used to perform!
Mom and I dressed a tiny bit rodeo appropriate without being too over the top. I think go with a hat OR boots if you’re not a true cowgirl and you’ll fit right in. I only had a bandana and vest with me, but wearing those with all black and sneakers helped me feel comfy but with just a nod to the event.
7 | On Hot Afternoons
Similar Tee | Bike Shorts (M) | Birks | Bag
A couple of days were pretty dang hot for Aspen (no AC in our airbnb) and I was glad to have another pair of comfy bike shorts (these from Quince are so soft but still hold you in) and an oversized tee. This combo is comfy to sleep in, too, if I hadn’t brought pjs, as well.
8 | Walking the John Denver Park Trail
Tee (M) | Shirt (M) | Sweats (M) | Nikes | Bag
On one of our last days we walked near the gorgeous Rio Grande River at the lovely John Denver Sanctuary downtown. I had stopped into Aviator Nation the day before and snagged some (sorry my pic doesn’t show the details better) Aspen specific sweatpants.
I adore their sweats so much so it was a nice souvenir. I don’t know if I would have invested had I not lived in a pair of their sweats last winter almost everyday, but since I had I knew I’d love them.
I know we’re heading into fall but with Aspen being a cool mountain town maybe this little outfit guide can be helpful as we ease into early fall. Or, sometimes, I think these travel posts are just fun to see what someone else did and wore on a trip…a little peek into life.
I’m so grateful to have gotten another wonderful summer trip with my dear family. Thank you Nonna and Papa John for the wonderful vacay! We rounded it off the last night even with family Olympics (the opening ceremonies were that evening in Paris) where the 4-year-old beat everyone with a variation on rock/paper/scissors. It was so awesome.
Here’s to family vacays, brothers, nephews, nieces, grandparents and gorgeous mountain towns!
xo,
L
You’re creasing the Dunks!!!