Stylish Winter Travel Outfits to Keep You Warm (While Still Looking Cool)

When snow boots will likely be your everyday footwear choice, you’ll want a pair you love lacing up in the morning. Try these waterproof boots by Sorel ($225; zappos.com) which are gorgeous and versatile. They’ll look great with tights and a dress, but also with dark-wash, skinny denim ($205; motherdenim.com), a casual flannel ($70; madewell.com), and a modern cable-knit sweater ($332; modaoperandi.com), with a belted trench ($365; jcrew.com) to cinch your waist. Add a leather bag ($128; madewell.com) to match your boots. It's the easiest way to make an outfit look thoughtful and complete. 

If you’re heading somewhere absolutely frigid, nothing tops the Canada Goose Kensington parka ($895; bloomingdales.com). When New York City brings out the big chill, you can’t walk a block without seeing someone in this down, water-resistant coat. With a high-neck sweater ($148; frenchconnection.com), cozy scarf ($45; loft.com), your favorite fitted jeans ($215; frame-store.com), and waterproof, insulated boots ($170; zappos.com), the cold weather stands no chance of slowing you down. Bring a backpack ($330; everlane.com) for easy wear with the parka.

You’ll feel extra prepared with a three-ways-to-wear parka ($549; nordstrom.com) that’s designed for wet and cold climates—we see you, Pacific Northwest. Wear it with a forest green mockneck ($98; madewell.com), medium-wash skinny jeans ($195; net-a-porter.com), and a scarf ($65; jcrew.com) that can double as a blanket on chilly flights. For extra traction, these North Face boots ($140; zappos.com) have temperature-sensitive lugs for excellent grip in extreme conditions. Just don’t forget your camp socks ($17; jcrew.com).

For a winter weekend trip to your neighboring city, stand out in a statement coat like this shearling-trimmed, boiled wool parka by Mr&Mrs Italy ($2,405; net-a-porter.com). Pair it with a super-soft wool turtleneck ($450; net-a-porter.com) and stretch skinny trousers to match the coat’s green accents ($142; farfetch.com). Leather accents like these cashmere-lined gloves ($155; neimanmarcus.com) and lace-up, faux-fur-trimmed boots ($375; stuartweitzman.com) will give you a little edge and a lot of warmth.

For a look that’s simultaneously warm and cool, pair a quilted down bomber ($70, uniqlo.com) with faded, grey denim ($128; madewell.com), a beanie ($38; neimanmarcus.com), and a shirt ($82; madewell.com) and scarf ($29; nordstrom.com) duo that mixes plaids with similar tones. For shoes, Cole Haan’s waterproof Chelsea boot ($95; 6pm.com) is just as suited to a museum tour as it is to a puddle-soaked walking tour.

Barbour’s thought-of-everything jackets have been keeping explorers warm for more than a century. This army green parka ($399; nordstrom.com) pairs well with a fair isle sweater ($60; mango.com), comfy stretch denim ($199; frame-store.com), and a twisted knit headband ($16; amazon.com/fashion). With a thick pair of socks ($9; ae.com), your winter boots ($120; nordstrom.com) can easily be traded for a pair of ice skates.

If you’re setting out for a day of boutique hopping or an evening out, this eclectic MSGM duster ($486; matchesfashion.com) is the perfect choice. Go for simple black basics underneath—a cashmere turtleneck ($135; everlane.com), mid-rise denim ($160; net-a-porter.com), and block-heeled, waterproof suede booties ($450; zappos.com). Add a knitted bobble hat ($95; shopspring.com) and a red lip to keep the look playful.

When heading out with a backpack ($110; amazon.com) full of camera gear in search of icicle-draped waterfalls, Uniqlo’s HEATTECH turtleneck ($10; uniqlo.com) and high-rise tights ($84; athleta.com) make excellent base layers for a long-length, down vest ($178; athleta.com). Flip-top fingerless mittens ($48; nordstrom.com) make it easier to operate your camera and rugged waterproof boots ($150; zappos.com) will help you get a closer look.

If the sidewalks are in good shape, but there’s still a chill in the city air, head out in a pair of color-blocked booties ($410; nordstrom.com) and MOTHER’s instant cool, frayed-ankle denim ($228; revolve.com). Complete the ensemble with a cozy cashmere-wool sweater ($98; everlane.com), fun blue leather gloves ($78; nordstrom.com), a neutral wrap coat ($905; matchesfashion.com), and a chain-strap cross-body ($195; nordstrom.com).

For a sunny, but brisk weather forecast, pack a reversible quilted gilet ($262; matchesfashion.com) and a chic pair of sunglasses like this matte black and ivory pair ($325; rag-bone.com) from Rag & Bone’s recent collaboration with Vuarnet. Stay warm with comfortable base layers like Moncler’s classic wool leggings ($245; farfetch.com), a marled pullover sweater ($50; llbean.com), and shearling-trimmed boots ($110; solesociety.com). Tie it all together with a color-blocked scarf ($13; hm.com).

Over-the-knee riding boots ($190; amazon.com/fashion) are another great high-style, low-temperature pick. Tuck in a pair of skinny jeans ($50; ae.com) and coordinate a color palette with your coat ($129; hm.com), scarf ($259; shopspring.com), and hat ($126; shopspring.com). A sweater ($80; jcrew.com) that matches too is just for extra credit.  

A winter day hike can be far more enjoyable with the right shoes and socks, like Forsake’s all-weather, premium leather boots ($150; amazon.com) and striped socks ($10; uniqlo.com) from Uniqlo’s innovative HEATTECH collection that’s designed to boost heat retention. For base layers, look for breathable, stretch fabrics like this capital-S soft Outdoor Voices hoodie ($85; outdoorvoices.com) and these extra-warm leggings ($15; uniqlo.com). For outerwear, a down vest ($149; eddiebauer.com) is easy to compress down and pack into your backpack ($45; nike.com) if you’re working up too much body heat on the uphill trek.

While a merino wool sweatshirt ($120; shopspring.com) and super soft tights ($130; ebags.com) are ideal loungewear inside the cabin, you can trade those cozy slippers for a pair of wool-lined hiking boots ($225; amazon.com/fashion) and zip up a wind- and waterproof down vest ($220; shopspring.com) to be ready for a snowshoeing trek around the mountain. Bring along an earband ($18; amazon.com/fashion) for added warmth and a backpack ($132; mytheresa.com) to store your gear and snacks for any winter adventure.

For a day of packing powder—with skis, snowmobile tracks, or an inflatable tube—you can’t go wrong with skiwear designed in the mountains of Switzerland. Capranea’s down-filled jacket ($1,060; matchesfashion.com), long-sleeved performance shirt ($129; matchesfashion.com), and waterproof trousers ($477; matchesfashion.com) will keep you on the slopes all day without want for warmth. Add some sleek boots ($650; rag-bone.com) and rose-hued aviators ($425; intermixonline.com) to complete the look.

For a winter hike that’s less push-to-the-summit, and more quick-poke-around-the-pines, keep it casual with a T-shirt ($15; uniqlo.com), jeans ($128; madewell.com), and a hooded parka ($60; hm.com). You should still treat your feet, though, and this pair of Merrell’s hiking boots ($225; zappos.com) blends all of their top-notch technical features with a throwback style. Bring out the red in the laces with a matching blanket scarf ($195; rag-bone.com) and convertible mittens ($150; nordstrom.com).

With some help from fleece-lined tights ($13; hm.com) and over-the-knee boots ($798; stuartweitzman.com), a corduroy mini skirt ($60; topshop.com) instantly becomes a bearable cold-weather wardrobe choice. When you have to cover up your embellished sweater ($350; shopspring.com) with a belted shawl coat ($265; everlane.com), pin on a playful brooch ($34; nordstrom.com) to bring the fun up a layer.

Packing in primarily neutrals—a black sweater dress ($118; madewell.com), black tights ($15; gap.com), a Chelsea boot ($175; everlane.com), and a camel coat ($350; jcrew.com), for example—is a simple strategy to maximize wear, but can start to feel a little boring. This is where patterned or brightly colored gloves ($185; neimanmarcus.com) and a scarf ($16; mango.com) can come in with bigger personality.

Before you stow your high-waisted culottes ($350; net-a-porter.com) for next summer, try them out with a cropped sweater ($268; intermix.com) and high, leather boots ($190; zappos.com). When heading out into the elements, grab a pea coat ($170; mango.com), cross-body bag ($160; shopbop.com), and some tech-friendly leather gloves ($50; gap.com). Add a floral pin ($12; nordstrom.com) for an extra hint of seasons past.