As a millennial, I often do what all millennials do on vacation—once I arrive, I spend the first few days, if not the whole trip, flirting with the idea of moving to that destination. It’s a mainstay in my travel routine. As annoying as the bit may be, it’s one that I refuse to shake.
For me, the most frequently talked about destination is Jackson, Wyoming. Every year, I return for a ski trip with my girls and every year I question whether or not I should pick up and move there altogether. While the conversation is mostly unserious, there is a small part of me that considers what life in the remote ski destination would be like. Ultimately what keeps me buoyed to life in Denver are the realities of Jackson’s harsh mountain town winter, re: getting bundled up from tip to tail every day to face below-freezing elements. To put it simply, I’m just not ready to up my layering game to that degree.
On vacation, however, it’s far more enjoyable. Since it’s not a daily occurrence, it feels more like a fun challenge, playing around with puffy and fuzzy layers until a comfortable, warm, and stylish outfit is found. It’s a delicate balance, but with the right packing list and cold-weather essentials, it’s more than achievable.
As a seasoned visitor, I know exactly what you need to pack to stay warm and look cute while vacationing in Jackson Hole and I’m happy to share my tricks of the trade with you. From what to wear on the slopes to what to wear around town, this guide will help you dress for the elements with ease.
Your Ski Trip Style Guide:
On The Mountain
My most recent trip to Jackson was for the Elevate Women’s Ski Camp where my bestie Maura and I spent four back-to-back days riding the resort and practicing skills with a professional coach. With more ski days on the agenda than usual, I packed two different snow pant and jacket sets to mix and match depending on the conditions of each day. If you’re skiing for more than a few days and have the luggage space, I’d recommend doing the same. On warm weather days, you can wear a lighter jacket, and vice versa on cold weather days. Plus, if anything happens to one set—let’s say, you spill hot cocoa on your jacket— then you have a clean backup to rely on.
What I Packed for Skiing:
- Jackets: Georgie Puffer in Black, Aston Jacket in Alpine Green
- Pants: Emma Soft Shell Bib Pant in Black, Isabel Soft Shell Bib Pant in Alpine Green (sold out in most sizes, but available in navy)
- Base Layers: Hallie Midweight Merino Set in Rust (Top and Bottom), Hallie Midweight Merino Set in Black (Top and Bottom)
- Mid Layer: Pieper Fleece in Oatmilk
- Accessories: Hestra Fall Line Mitt, Marquis Polartec® Fleece Neck Warmer
What I Wore While Skiing (and Après-ing):
Skiing Outfit Perfect For: Cold Groomer Days.
Conditions: Negative temperatures and no new snow overnight.
The plush fleece combined with the thick puffer jacket provides the insulation you need on frigid ski days. I’m typically a bibs-over-pants girlie because I’m always afraid of getting snow where the sun don’t shine, but on days where there’s no fresh snow overnight or forecasted during the day, pants are a safe bet! The fleece neck warmer and leather mittens were a mainstay in most of my outfits because they are suitable for almost any type of ski day.
Skiing Outfit Perfect For: Coldish Powder Days.
Conditions: Under 20 Degree Temperatures with Fresh Snow
Details: Isabel Soft Shell Bib Pant (sold out in most sizes but available in navy), Georgie Puffer, Hallie Midweight Merino Set in Black (Top and Bottom), Hestra Fall Line Mitt, Marquis Polartec® Fleece Neck Warmer.
When the temps start to warm up, but it’s not quite a bluebird day, I recommend ditching your mid layer but keeping a puffer. With a layer of fresh snow, your body will be working hard enough to generate plenty of heat and keep yourself warm.
Skiing Outfit Perfect For: Warm (& Heavy) Powder Days
Conditions: 30 Degree Temperatures and Lots of Fresh Snow
On days when it’s warm on the mountain and there is a lot of fresh snow, you’ll want to keep your layers as light as possible. Skiing through heavy snow requires a lot of effort and thus you’ll be working up a sweat. Combine that with above 30-degree temps and you’ll really be glistening. On days like these, I ditch my mid layer, opt for a lighter snow jacket, and stick to my bibs (re: keeping snow out of my pants).
Skiing Outfit Perfect For: Sitting on a Patio or By the Fire at a Lodge
There comes a point in any ski trip when your legs just can’t take it any longer. When that day inevitably comes, as it did on the fifth day of my trip, you can still look the part while enjoying yourself at Après. Simply skip the base layers and mid layer, and opt for a comfy shirt to go with your ski pants and jacket. I accessorized my outfit with a sporty fanny pack, chic sunglasses, fuzzy hat, and silver earrings. The snow boots I wore that day, and every day of the trip, were perfect because a) they looked cute with my outfit(s) and b) they are possibly the most comfortable snow boots known to woman.
Bopping Around Town
Despite the reputation for hosting billionaires, Jackson is still a somewhat casual town. While it’s no stranger to extravagant fur coats and expensive puffer jackets, you’ll also see people out at night still wearing their ski clothes from the day. All this to say, it’s your choice how dressy you go— either way, you’ll fit in.
My biggest piece of advice is to pack staples that are easy to mix and match. I loosely used the 3-3-3 packing method—packing three easily mixable options for each category: pants, shirts, accessories, and shoes. Again, I didn’t follow this method completely (there should be exceptions for cold weather destinations) but it did serve as inspiration for what I wore.
What I Packed for Exploring the Town:
- Pants: Old Navy Baggy Jeans, Citizens of Humanity Light Wash Baggy Jeans and Black Leggings
- Sweaters: James Street Co. Sloane Vee Sweater, Vintage Cowichan Sweater, Halfdays Pieper Fleece
- Essentials: Aritzia Sinch Smooth Willow T-Shirt, Aritzia BestHug™ Little Ribbed Longsleeve
- Accessories: Topo Designs Fanny Pack, Fifth and Ninth Lucia Plush Bag, Halfdays x Matek Mot Mot Balaclava, Tio Lee Fargo Hat, Fifth and Ninth Taya Sunglasses
- Shoes: Fubuki Niseko Boots (I packed two other pairs of shoes but only ended up wearing my Fubukis because there was so.much.snow.)
- Outerwear: Wheeler Parka— this oversized red puffer looked good with EVERYTHING.
What I Wore While Exploring the Town:
Jackson Hole Outfit Perfect For: Shopping in Town
Part of the reason why I love Jackson Hole so much is due to its casual vibe—jeans and a sweater are pretty much appropriate anywhere you go. For shopping in town, I wore these light wash jeans (uncuffed) and an oversized v-neck sweater. I also wore this out to dinner that night—who said day-to-night dressing wasn’t relevant? The sunglasses, handbag, boots, and parka went with nearly every outfit I put together that week, making my styling job easy!
Jackson Hole Outfit Perfect For: Dinner and Drinks at The Million Dollar Cowboy Bar
For a fun night out at The Cowboy Bar, I loved wearing a vintage Cowichan sweater (almost identical to this one) with baggy jeans and a basic white tee shirt. Of course, the bag and Niseko boots had to accompany this ‘fit too.
Jackson Hole Outfit Perfect For: A Snowy Night out at Teton Tiger
When it’s snowing like crazy, I love to wear my Mot Mot Balaclava out to keep my hair dry and my face warm. Since the balaclava is already a statement piece, I keep my essentials pretty basic with dark wash jeans and a black long sleeve. Paired with the bright red parka and voila— the perfect winter outfit does exist.
Jackson Hole Outfit Perfect For: Slow Mornings Grabbing Brunch in Town
On slow mornings, I always reach for my fuzzy fleece jacket. It’s warm enough to be worn skiing and stylish enough to be worn with jeans— what more could you ask for? On a warm day, pair it with sunglasses, earrings, and a cute fanny pack and you’ll be ready to (comfortably) take on the day.
Jackson Hole Outfit Perfect For: Traveling Home (sob)
On travel days, comfort is my number one priority. For our return trip to Denver, I wore leggings and a white tee but kept some of my favorite accessories on for our final morning in Jackson. With one last brunch walk to Persephone, this cowgirl was back to reality.