Stylish Winter Travel Outfits to Keep You Warm (While Still Looking Cool)
When traveling during the winter, it can be tempting to leave behind slush-soaked sidewalks and cheek-scorching winds for sunny skies and an easy ocean breeze. But there are so many places that are strikingly beautiful—and far less crowded—during the colder months. Aside from ski resort towns, there are generous off-season deals to be found all throughout Europe, and the long weekends in January and February are perfect for a short, snowy getaway close to home.
But more so in winter than any other time of year, packing smart is essential. Do your research to see just how low temperatures could drop, and if you’re sensitive to cold, bring a big, warm coat instead of trying to layer yourself into immobility. You can always tuck it into the overhead bin if you don’t want to wear it on the plane, though (believe it or not) it's possible to pack a heavy winter jacket.
Sneakers always make for comfy travel shoes, but they're not as useful in the face of a wintry mix. If there’s even a chance of chilled precipitation where you’re headed, invest in sturdy, waterproof boots with good traction and room for a thick sock. Warm, dry feet can be the difference between a fun, active day and one that’s reduced to the time you spent as a sad, human-shaped ice cube.
Yes, winter boots tend to be bulky—even the cute ones—and are admittedly a pain to take off at airport security. But don't let that deter you. Boot removal amounts to no more than a cumulative 15 minutes of your trip, accounting for very complicated boots, whereas you’ll be spending hours on end braving the elements. If you do decide to pack a pair, stuff them full of smaller items to save room.
In addition to the essential winter accessories (gloves, scarves, a hat) consider bringing a few pairs of leggings or tights that are opaque, preferably fleece-lined, and can be worn comfortably underneath a pair of pants if needed. It’s also more convenient to forgo a tote or handheld bag for something no-fuss, like a backpack or a cross-body.
And the best way to wear all of these essentials without entering blob territory? Coordinate your outerwear, and keep the base layers basic with neutral sweaters, easy-to-layer tops in heat-retaining fabrics, and denim. Below, you’ll find winter travel outfit ideas that are warm, versatile, and very decidedly not marshmallow-like.
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.