Winter is by far the most difficult time of year to pack for. Bulkier apparel is certainly necessary to stay warm in snowy, cold destinations, but those thick fleeces and burly snow boots take up prime real estate in that good ol’ carry-on bag. Instead of caving and giving into the temptation of checked baggage, check out these layerable, space-saving, functional and fashionable travel pieces that will keep you warm and looking good, whether you’re hiking through the airport, or après-ing it up around town.

 

Chaco Women’s Cataluna Mid

The stylish Cataluna Mid’s are an excellent, durable and waterproof piece of footwear for rainy fall weather that turns into slushy snowstorms. These ankle boots are perfect for trips that require both casual and dressy activities — and they’re incredibly comfortable to boot… A full grain waterproof leather upper makes the Cataluna’s a versatile pair of boots capable of tackling whatever Mother Nature throws your way. A removable dual density LUVSEAT™ EVA footbed offers excellent support, and will keep your arches comfortable, even throughout long days of exploring cities or new towns. If you’re looking for something a little more casual, and without the heel, check out Chaco’s Women’s Sierra Waterproof boots. These super cute boots are rugged enough for winter weather, and are equipped with enough traction on the sole to stand up to icy terrain.
$180; chacos.com

prAna Cozy Up Sweatshirt

This sweatshirt more than lives up to its name. The Cozy Up Sweatshirt is a glorious blend of hemp, recycled polyester and ultra-soft fleece. It’s UPF 50+ and made up of natural odor-reducing materials, which makes it a hardworking piece that will hold up to multiple uses during your trip. The Cozy Up is incredible soft, and boasts a relaxed fit that you’ll especially want to rock on a busy travel day. It’s modern take on a vintage design transcends the typical idea of a boring sweatshirt, and instead, is a great casual piece that you’ll want to wear while out exploring restaurants, or even when you need to warm up after a day on the slopes. Plus, when you purchase threads from prAna, you’re supporting the company’s commitment to sourcing sustainable materials for their clothing, which will make you feel even more warm and fuzzy inside when you don this sweatshirt.
$79; prana.com

Toad&Co Women’s Serape Stripe Scarf

Eye-catching accessories are the best way to make the most out of each piece of apparel in your suitcase. Mix and match pieces in your small arsenal of clothing, and jazz it all up with this beautiful (and warm!) scarf from Toad&Co. This infinity scarf is made up of 60 percent wool and will tie any outfit together — which is perfect when you’re trying to stretch your suitcase wardrobe as far as it will go. When it comes to fashionable, yet highly functional and well-made lifestyle wear, Toad&Co makes some of the best around.
$52; toadandco.com

Mountain Khakis Women’s Genevieve Skinny Jean

If you’re like me, a classic pair of skinny jeans is a staple in your travel wardrobe. Skinny jeans can easily be dressed up or down to fit wherever the day takes you, and Mountain Khakis’ new Genevieve Skinny Jean is made with an organic cotton material that is so comfortable, you’ll want to wear them everywhere you go. It’s easy to see why these jeans are a bestseller for the brand. They’re hardy, and will withstand a lot of wear; and subtle design touches like embroidery on the pockets designed to mimic the Tetons give these classic Western-style jeans a nice fashionable touch. $84.95; mountainkhakis.com

Helly Hansen W Lifaloft Hooded Insulator Jacket

The warmth-to-weight ratio on Helly Hansen’s Lifaloft Hooded Insulator Jacket is everything you could ask for when finding an excellent, one-stop shop winter jacket. Not only is the design sleek enough to take you from the trail to the tavern, but it’s crazy warm and at 350 grams, only takes up about the amount of room in your travel pack as a long sleeved shirt. The cornerstone of this jacket is HH’s revolutionary Lifaloft™ technology — a combination of Lifa yarn technology that traps more air than polyester at a lighter weight, and PrimaLoft® synthetic insulation. It’s windproof, water-resistant, and produced at a lower impact to the environment than polyester. $230; hellyhansen.com

Costa Del Mar Sunglasses

There are so many types of sunglasses designed for specific activities and all different types of lighting, but I’m always on the hunt for a durable pair of shades that will perform equally as awesome throughout all parts of my travels. Whether I’m playing outside, attending a wedding, or putzing around the city, I want one pair of go-to shades, and Costa’s Del Mar collection has become a fast favorite of mine that fits all of my needs. For starters, I love the look of Costa’s Del Mar sunglasses. The laid-back lifestyle-inspired frames come in a variety of designs, and the polarized lenses are available in a seven different lens colors that range from low-light like dawn, to extremely bright light with blinding glare. Like all of Costa’s lenses, the Del Mar’s scratch-resistant glass lens also provides exceptional clarity. $249; costadelmar.com

Duluth Trading Co. Lifetime Leather Travel Duffle Bag

The Lifetime Leather Travel Duffle Bag by Duluth Trading Co. is like a Mary Poppin’s bag. At 14-1/2 inches by 19 inches by 9 inches, it’s an incredibly spacious bag. If you prefer to travel light, and typically opt for a duffle as your one carry-on bag, this leather duffle is an elegant and classy version that still provides the type of roominess and ease-of-carry that you desire. Its rugged exterior is comprised of 100 percent oiled full-grain leather. Inside of the roomy interior are three bellowed pockets and one larger zippered pocket to help you stay organized. The Lifetime Leather Travel Duffle Bag will also technically fits under the airplane seat in front of you (although its less likely to do so if you pack it to the brim), so you can travel with all of your goods at all times without having to succumb to the checked baggage line. $269.50; duluthtrading.com

FITS Women’s Zig-Zag – Crew Socks

Whether you’re trekking through the airport, or through the quaint downtown area of your favorite mountain town, a warm pair of wool socks is key. But any old sock won’t do. An ill-fitting, thin sock can crush your spirit during long days on your feet, which is why FITS’ patented Full Contact Fit®, which snuggly hugs your feet and keeps your socks in place, is an ideal choice. FITS is known for making some very comfortable merino wool socks for hiking, but their line of lifestyle socks pack in just as much technology with cute designs suitable for everyday wear. $19.99; fitssock.com

LifeStraw Special Edition LifeStraw Go

Having an easy, transportable way to filter water, wherever your adventures take you, is crucial for every traveler. LifeStraw’s Go is a two-stage filtration refillable water bottle that removes 9.99 percent of waterborne bacteria and protozoan parasites as well as microplastics. It’s BPA-free and pretty darn tough. It holds 22 ounces of safe drinking water, and the filter is replaceable, which means you won’t have to buy an entirely new bottle once you’ve hit your filtration max. The award-winning company recently launched a special edition “Big Adventure” bottle which not only features a cute design, but also helps protect wild places with five percent of the purchase of each bottle benefiting The Conservation Alliance. $44.95; lifestraw.com