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Tackle any type of terrain with these tips.
Whether you’re headed to a snowy locale to do some stylish skiing or just visiting a city with some chilly temperatures, packing for a cold-weather vacation can be tricky. Boots, slippers, and heels take up more room in your suitcase than flip-flops or mules you might wear someplace warmer. But with a little work, you can find the right balance between fashion and function.
“Choose boots that keep your feet dry and warm on snowy terrains and look for non-slip soles for added stability on uneven surfaces during potentially icy-coated walks and chilly adventure explorations,” says Ginnie Bond, president at luxury footwear brand Donald Pliner. “To travel light, pack no more than three pairs of shoes: a durable walking boot, a versatile indoor option, and a polished style for dressier occasions,” she adds.
If you're gearing up for a big trip and need advice about what footwear is perfect to bring along, read on.
What to Look For in Vacation Footwear
Don’t bring shoes you’ve just bought. Make sure you bring styles you already own or wear a new pair for a few weeks before your trip so you’re guaranteed a comfortable stride. And look at the materials carefully. “Opt for waterproof materials like Gortex and thick insulation to keep your feet warm,” says Tara West, award-winning fashion stylist, adding, “Think about the height of the boot. If there’s a lot of snow, choose a boot that is knee-high, and if the snow’s light, choose a boot that’s ankle-high. Look for buckles or laces to keep it snug.”
You’ll also want to think about weight. “Shoes that are lightweight, flexible, and cushioned ensure all-day lasting wearability, especially for sightseeing,” says Bond. In the same vein, pick shoes that are multifunctional, whether that means neutral tones like black and brown or a classic, knee-length style. Mary Alice Malone, creative director at inclusive boot brand DuoBoots, suggests considering how they’ll look and feel styled in different ways, going for silhouettes that have a wide range of heights and calf sizes.
Boot sizing can be tricky, so try them on with a heavy pair of socks. "You might need to size up a half or full size in some boots," explains West. The same goes for pointed-toe shoes: "Consider a half size up for added toe room while maintaining the shoe’s tailored silhouette," says Bond. But with loafers or slip-ons that don't require extra room, "Stick to your true size for a secure fit."
The exact shoes you pack will depend on the context of your vacation. You probably don't have room for all these items, but they're good options for packable, versatile shoes.
A Comfortable Boot
“If you’re going skiing, you should wear an après-ski boot, such as a Moon Boot, or something slightly [more] fashionable for drinks on the slope,” explains West. If space is tight in your suitcase, she adds: “Consider packing one après-ski boot that you can also use for daytime walks and lunches.” A slip-on design like this, with a rubber sole with suction pads, insulated inner, and water-resistant nylon outer, is multifunctional: you get warmth and traction in snow and rain, but they also feel fashion-forward. They go well with ski pants, denim, and leggings equally well. If you’re going for a more heavy-duty boot, opt for Sorel, Mukluks, REI, or Merrell snow boots.
A Waterproof Boot
While snow boots are helpful for outdoor activities, “waterproof boots are practical for snow and slush,” says Stitch Fix stylist Jordan Walker. Brands like Hunter, L.L.Bean, Xtratuf, and Merry People offer wellies and rain boots that combine comfort with water protection. Short boots are easier to walk in, whereas a higher knee-high silhouette “lends an extra layer of warmth,” says West. Because rubber can leach heat and thus make your feet colder, “look for linings, padded insoles, or leather construction to retain warmth and provide maximum durability in snow or rain,” explains Bond. Citing that some of their brand’s boots offer water resistance, she adds: “Opt for durable rubber outsoles or lite-lux EVA rubberized foam soles with tread patterns to reduce slips on icy surfaces.”
A Simple Shoe or Pump
A classic is a classic for a reason. “[A pair of pumps] perfectly complements a winter coat, long dress, and fleece-lined sheer tights, creating the perfect ensemble for a sophisticated dinner, New Year’s Eve celebration, or holiday get-together,” explains Mario Silva, art director of luxury shoe brand Bruno Magli. If a high heel is too much for you, especially in rough or uneven terrain, a smaller heel is “a sophisticated look as an alternative to high heels,” he adds. Plus, they’ll fit into your suitcase more easily! Alternatively, a polished loafer can have the same effect if you’d rather not wear a heel. “Pair them with tailored pants or leggings for an effortlessly stylish look,” he adds. The brand works in Italian leather, meaning they can stand up to the elements without waterlogging or falling apart.
Black Boots
There's a variety of classic black boots available, depending on your style. Perhaps it's a low pair: "I love an ankle boot because they’re compact enough to fit in a carry-on or weekend bag and can elevate an outfit for a nice dinner, making them multifunctional and perfect for on-the-go trips," says Walker. With a chunky block heel, Silva says: "[They] complement both semi-formal and casual looks and offer a stylish alternative to heels for a night out or an upscale dinner. Pair them with a skirt and fleece-lined sheer tights for a cozy yet elegant look, or wear them with your favorite pair of jeans and a sweater for a casual, elevated style." A faux fur-trimmed boot is a nice up-level from your classic pair, explains West, and would even work for a fancy dinner or other upscale event.
Cozy Boots or Slippers
It’s actually kind of brilliant: bring along your coziest slippers or casual boots, both for light walking excursions and also for the impressive amount of lounging you’ll be doing. “To walk around town and window shop, you can style Ugg boots or something lined with warmth that also looks cute with a snow hat and a puffer jacket,” explains West. What’s great about Uggs and slippers is that they’ll take up less room in your suitcase, or they’ll be the perfect footwear for a long plane or car ride. If these are too casual for you, Bond cites these brands’ slip-on shoes as a nice and slightly more elevated option: “Equal parts slipper for comfort and sneaker-esque tread for traction.”
Something Eye-Catching
If style is an important part of your aesthetic, choose footwear that makes a major statement. This might be less practical than a waterproof shoe or boot, but could instead be a statement piece that looks trendy but still feels comfortable. “Try a western-inspired boot, perfect for the Ranch Revival trend Stitch Fix predicts will take off in 2025. For a night out on a cold-weather vacation, consider a snake-skin boot. In Stitch Fix’s 2025 Trend Report, we saw a 400 percent increase in requests for animal print this year,” explains Walker. Or, if you want something more classic, choose “a go-to equestrian boot: classic, low-heeled, with a rubber sole for all-weather ease. The buckle and strap add a chic biker edge. I love pairing it with a long skirt and a cozy jumper for a contemporary look,” says Malone. If you want to combine function and fashion in one shoe, go for fashion sneakers like New Balance or Everlane.
How to Pack
Get a good sense of the weather conditions before you pack. "Not all winter destinations are created equal, so it’s important to know the temperatures of your location before you go," explains Bond. She also suggests: "Check the forecast not only while packing, but also as you actually dress in preparation to step out for the day ahead."
The pairs you pack should serve multiple functions and go with all your outfits. "If you're someone who likes versatility and wants to pack a lot of footwear, I suggest wearing your Ugg boots on the plane to take up less space packing," says West. Adds Bond: "Consider bundling smaller winter accessories together, like hats, scarves, and gloves to place inside of shoes to allow even more space-saving room."
It's also worth noting that boots can get dirty easily and thus might contaminate the rest of your suitcase. "Before packing, make sure shoes are clean to prevent gritty grime from transferring to other items. Packing cubes help separate shoes while keeping items neatly organized," says Bond, adding, "Spray boots with a water-repellant spray before packing for extra protection and peace of mind because surprise slush puddles happen."
If you wish you could pack more, or that your winter-ready shoes were a bit more exciting for your getaway, "a fun way to personalize your look is through accessories like bold laces or printed socks peeking out of boots," adds Walker. "This lets you stay stylish and weather-ready without compromising functionality."