Is anyone surprised that I’ve already taken a trip to Jackson Hole this year? I mean, I did wait a couple of weeks at least! If you have been following me for a little while, you’ve probably picked up on my love for traveling to Jackson Hole, Wyoming by now. It’s true, Tim and I love to venture off to our favorite travel spot often, and we aren’t too partial about the time of year. However, this time around we decided to make our winter trip to Jackson Hole a ski trip, which required a lot more gear to pack!

As you read through this blog post you might notice that I packed my bags with a whopping 14 outfits – yeah, my luggage was definitely on the heavy side, but totally worth it. Also, I haven’t hit the slopes in 17 years, so I’m crossing my fingers that skiing is like riding a bike and it all comes back to me. Either way, I know we’ll have a blast soaking up all that Jackson Hole has to offer! The place is just lovely, with the outdoors being all jaw-dropping. Another bonus is that the town is so much fun for shopping and grabbing some delicious meals. In this post, I’m rounding up all the details of those 14 outfits in case you have a winter trip to Jackson Hole, or somewhere similar, planned. So, let’s jump in!

What I Packed for a Winter Trip to Jackson Hole

shopping around town square

Okay, picture this – strolling through Jackson Hole’s charming town square, looking like a winter fashion maven. For some laid-back shopping vibes, I’ve got my faux fur coat to stay cozy, paired with a chic beige fair isle crewneck sweater. Rocking those high-rise ’90s relaxed jeans in a cool bone color, and keeping my feet dry with faux shearling trim waterproof boots. Of course, I’ve got leather gloves to combat the chill, a tan belt for that extra touch, and a felt western hat to add some flair. Topped it off with classic pearl stud earrings and my favorite lipstick – because why not?

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ski day

To hit the slopes in style, I packed a houndstooth down puffer ski jacket that’s as warm as it is chic. I paired it with crisp white ski pants and a snug baselayer crewneck long-sleeve top to stay toasty. Gotta keep those feet comfy with cushioned ski socks, and safety first with a white ski helmet and ski goggles. My hands were covered with insulated ski mittens, and I’m all about sun protection with face and lip sunscreen because you can get a bad sunburn during a long day of skiing! Then, I tossed on my favorite waterproof mascara so it would last all day. And of course, can’t forget the details – pearl stud earrings and my trusty belt bag. I was ready to conquer those peaks in style!

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If you’re heading on a ski trip soon, check out this post on what to pack to stay warm on the slopes!

hotel lounging

This might just be the ultimate in hotel lounging comfort outfit for resting after a long day out on the slopes. I’ve got this dreamy long-sleeve henley and jogger lounge set that’s basically a hug in clothing form. Tossed on some cashmere-blend socks for that cozy feel – because who doesn’t love a bit of luxury? And we can’t forget a pair of Ugg boots, perfect for both comfort and style. Packed my Kindle Paperwhite for some cozy reading sessions, and essentials like Revision lip balm and the best nail-care cream for a touch of pampering. Hotel lounging has never felt this good!

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dinner in town

Dinner in Jackson Hole calls for a mix of style and warmth, right? I packed this chic faux fur coat that’s not just cozy but also a serious head-turner. Paired it with a ribbed turtleneck top for that extra snug feel and high-rise ankle flare jeans – because, you know, gotta keep it trendy. Stepped into leather booties, slung a quilted leather bag over my shoulder, and added a silk scarf for that touch of sophistication. Finished the look with classic pearl stud earrings and my favorite lipstick because sometimes dinner vibes deserve a bit of glam!

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dinner date in Jackson

Alright, picture this cozy-chic vibe for a dinner date in Jackson Hole. I packed this faux leather and wool zip-up coat – it’s warm, stylish, and basically a winter go-to. Pair it with a snug ribbed turtleneck top and high-rise ’90s relaxed jeans in a bone color. Then, I stepped into leather booties for that extra edge and slung a quilted leather bag over my shoulder. Don’t forget leather gloves to keep your hands warm! I added a touch of glam with gold boot-shaped earrings, because why not? And, of course, I’m finishing off the look with my absolute favorite lipstick.

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APRÈS ski

When it’s finally time for the ultimate après ski chill vibes in Jackson Hole, this outfit is perfection! Picture me cozied up in a faux fur coat, because, let’s be real, après ski style calls for an extra touch of glam. Pair it with a ribbed turtleneck top for that snug feel and faux leather leggings – comfort meets chic. Stepped into Ugg boots for that après ski classic look, and of course, gotta keep those hands warm with leather gloves. Tossed on white earmuffs for a playful touch and my favorite sunglasses. Slung a quilted leather bag over my shoulder, and to top it all off, my absolute favorite lipstick – ’cause who says you can’t be stylish off the slopes too? Ready to unwind in style after a day on the slopes!

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travel day

Alright, let’s talk about the comfiest travel day outfit for my winter trip to Jackson Hole. Picture this: a half-zip hoodie – cozy and easy, paired with leggings for that ultimate comfort. Stepped into Ugg boots, of course, because travel days call for maximum coziness. Slipped on cashmere-blend socks for that extra layer of warmth. Added a touch of elegance with classic pearl stud earrings. Tossed in my essentials – Revision lip balm, and Kindle Paperwhite for some in-flight reading, all neatly packed in a large tote bag. And, of course, can’t forget my trusty BÉIS roller bag for easy and stylish maneuvering through the airport. Ready to tackle travel day with comfort and a hint of sophistication!

I also highly recommend visiting Jackson Hole with family! See this post for my Jackson Hole travel guide.

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dinner in Jackson

Alright, let’s talk dinner vibes in Jackson Hole. Picture this: strutting into town with a faux fur coat that’s basically a warm hug in chilly weather. Pair it with a beige fair isle crewneck sweater for that cozy-chic feel, and high-rise ’90s relaxed jeans in a bone color. Step into leather booties to keep it sleek, and of course, leather gloves to ward off the winter chill. Add a quilted leather bag to carry all of your essentials. Throw on a pair of sunglasses to block out the sun before it goes down, add a pair of classic pearl stud earrings, and seal the deal with a swipe of lipstick.

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waffles at Corbet’s

Why yes, I do have an outfit planned for some waffles at Corbet’s in Jackson Hole – because breakfast deserves a stylish moment too! I’ll be cozied up in a goose-down puffer jacket, paired with faux leather leggings for a comfy yet elevated look. Add white faux fur boots because, well, why not make a statement with every step? I also plan to be wrapped up in a scarf and I’ll also add a cute pink knit beanie because I gotta keep warm in style. I’ll be sporting insulated mittens to combat the chill and sunglasses for the morning sun. I love to add classic pearl stud earrings and a swipe of Dior Addict Lip Maximizer for a touch of glam.

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million dollar cowboy bar

Gear up for some Western vibes at the Million Dollar Cowboy Bar in Jackson Hole – I’ve got the perfect outfit for that rustic-chic charm. Imagine rocking a faux leather and wool zip-up coat – stylish, warm, and just right for the cowboy ambiance. Pair it with a snug ribbed turtleneck top and high-rise ankle fray jeans – comfort meets a touch of trendiness. Cinch the look with a tan belt and throw on a felt western hat for that extra cowboy flair. Step into leather booties and add a pair of gold boot-shaped earrings for a playful touch, and of course, a swipe of lipstick to complete the look.

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travel day

Let’s talk travel day essentials for a winter trip to Jackson Hole! I’ve got the ultimate comfort combo – a cozy goose down puffer jacket paired with a half-zip pullover. My biggest travel tip is to always wear your biggest coat on the plane so that you don’t have to make room for it in your bag! Then, I added this pair of matching sweatpants for that laid-back vibe, and of course, stepped into Ugg boots because, well, travel days are all about maximum comfort. I threw on my favorite sunglasses, added classic pearl stud earrings, and made sure to keep my lips hydrated with Revision lip balm. I tossed all the essentials into a large tote bag and, of course, my trusty BÉIS roller bag for easy maneuvering through the airport.

Curious to know what I really think about my BÉIS carry-on bag? See this post!

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granite hot springs

Get ready for some serious winter relaxation at Granite Hot Springs in Jackson Hole – and you bet I’ve got the perfect outfit for that. Imagine being bundled up in a snug goose down puffer jacket, ready to embrace the warmth of the hot springs. Beneath that, keep it cool and chic with a black bikini top and bottoms – because why not? Step into white faux fur boots for that après ski flair, and topping it off with a playful pink knit beanie. Throw on sunglasses for that poolside cool factor and keep your essentials close with a handy belt bag. Waterproof mascara? Check. Tinted sunscreen for that mountain sun? Double-check.

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APRÈS ski

Alright, let’s talk après-ski vibes in Jackson Hole – and I’ve got the perfect outfit for that cozy-chic post-slope relaxation. Try a snug goose down puffer jacket, paired with a black oversized tunic sweater for that laid-back après-ski feel. Add some faux leather leggings for a touch of edge and step into faux fur boots because, well, après-ski should always be stylish. Top it off with a playful pink knit beanie, white faux fur mittens for extra warmth, and a chain quilted leather bag to keep things practical. Add a pair of classic pearl stud earrings and sunglasses for that après-ski cool factor. Finally, seal the deal with a swipe of Dior Addict Lip Maximizer.

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spa day

Prepare for the ultimate relaxation at the spa in Jackson Hole with this outfit. First, start with this luxe faux fur coat – because, why not make spa days stylish, right? Pair it with a quarter-zip fleece pullover and comfy leggings for that ultimate coziness. Stepping into Ugg boots and cashmere-blend socks for an extra layer of comfort. Top it off with a snug knit beanie, because spa days call for a touch of warmth. Don’t forget your essentials – tinted sunscreen, Revision lip balm, and of course, sunglasses for that post-spa glow. Add a hint of elegance with classic pearl stud earrings.

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So there you have it – the lowdown on what I packed for my winter trip to Jackson Hole! From chic dinner outfits to cozy après-ski looks and spa day essentials, it’s been a journey of style and comfort. Now, go hit those slopes, savor the town vibes, and soak up every moment this winter wonderland has to offer.

Which outfit is your favorite from what I packed for a winter trip to Jackson Hole? Let me know in the comments!