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Young black woman drinking coffee wandering in the streets of Madrid on winter tourist
David Prado Perucha/Shutterstock

How to Pack for a Winter Vacation

If you read travel publications and trawl the web for packing tips, you can find millions of words of sometimes commonsensical, sometimes scolding, and generally somewhat vague advice on how to pack for a winter vacation. Don’t pack too much stuff, dress in layers, pack a hat and gloves—but you know all that stuff already.

To help convert general packing advice into a usable packing list, I have some tricks you can use to help figure out where to start. We’re not talking about packing for a ski trip—that is its own special challenge—but most travelers should find these winter travel packing tactics simple, straightforward, and useful for a more general vacation.

Hats—the Secret to Staying Warm

carhartt winter black beanie.

Back when I used to go to concerts that weren’t scheduled on Saturday mornings at 11:00 a.m., I went to a lot of concerts, year-round, mostly in the northeastern U.S. Wearing bulky clothes into a music bar, concert hall, or jazz club isn’t that different than doing the same on an airplane. I learned that a light fleece and a warm hat were all I needed to get from car to club, through the line, and back again without freezing on a city street in February—the same goes for sprints through airports, short walks for breakfast in the morning cold, and more. If you don’t want to freeze your bum off, wear a good hat.

Requirements for a good travel hat:

  • Covers your ears
  • At least partly covers the back of your neck
  • Has no flaps, fluffballs, or other wasted mass
  • Is made of thin, modern materials for maximum warmth

There is nothing quite so brutal as a freezing-cold noggin, so if you choose one item very carefully, make it your hat. Amazon offers numerous options, such as this Carhartt watch hat for men or this fleece cap for women.

Shoes—Your One Heavy Item

Merrell Moab Adventure Chelsea Polar Waterproof.

Given that your feet are on the front line of most weather you will encounter, this is the one area that I recommend you be unafraid to go big. A solid, decent-looking pair of low-frills winter boots that you wear right onto the airplane will come through for you again and again during a winter trip.

Requirements for good winter travel shoes:

  • Weatherproof—Gore-Tex gear can be pretty styling these days
  • Light on lacing—you still need to get through security, so a pair of shoes or boots that can be worn loosely and don’t require a lot of tying and untying will help
  • Dark, so they won’t show stains from mud, slush, or getting thrown on filthy security belts

There are plenty of decent boots that hold up well enough to hike through snow in, but look good enough to wear to dinner; find them and wear them when you walk out the door for the airport. Examples include this option for women and this pair for men.

Gloves—Thin, Light, Breathable, and Waterproof

Glacier Glove Perfect Curve Glove.

The days of massive mittens and wool gloves are gone, at least for smart travelers; you can get a great pair of warm, waterproof, yet very thin gloves that weigh only a few ounces and take up only a few square inches of your luggage. The breathability makes them wearable across a wide temperature range, the waterproofing makes them useful in the worst weather, and the tight packaging makes them very low impact both when packing and when carrying them around.

Requirements for travel gloves:

  • Weatherproof
  • Breathable
  • Extremely light and low bulk
  • Quick-drying
  • Have some type of grip

Consider this option from Glacier Glove. Between your hat, boots, and gloves, your vulnerable extremities are covered.

Clothing—Morning Paper Trick for Layering Up

Amazon Essentials Women's Full Zip Polar Fleece.

Almost every collection of tips on how to dress/pack/stay warm/etc. in winter includes advice to dress in layers—which sounds great, but how do you go about it? Where do you start, and where do you stop? Without a plan, you could layer yourself up until you look like the Michelin man. To get a handle on how to pick and choose from the clothes you already own, try this trick.

When traveling during winter, use a “morning paper” approach to figure out what to pack:

  • T-shirt for reading the paper indoors
  • Long-sleeve top over that for grabbing the paper from the stoop
  • Fleece (or sweater, though wool tends to be bulky) over that for getting the paper from the curb
  • Light wind- and waterproof outer shell over that for getting the paper from the curb in the rain

If you pack such that you can get the paper in any weather, and then add and remove items as you go in and out of doors, you will have enough and the right clothes to layer up for pretty much any weather you will encounter, indoors or out.

Some Accessories to Consider

Wander Agio Women's Fashion Long Shawl.

Polarized sunglasses: Even weaker winter sunlight, when reflected off snow, can be rough on your eyes. In addition, the sun is lower in the sky, so is more likely to be in your line of sight or become a problem when driving during the short daylight hours. In those conditions, polarized glasses perform extremely well.

Sunscreen: Sunscreen in winter? Absolutely. A sunburn from reflection off of snow or ice is every bit a rival of a summer sunburn.

Lower-body base layer: If you are going to be spending extended time outdoors, consider packing a base layer to keep your legs comfortable in the cold. They are harder to shed than a top layer, but don’t take up much packing space and are essential if you’ll be outside for hours at a time.

In harsher weather, a scarf can be a small and light but very effective addition.

Resist the Urge to Pack Your Favorite Gear

I have an oversized black wool jacket that I would take around the world if it didn’t weigh about eight pounds and take up enough space to half-fill a suitcase. Every winter trip I look at it and think, yeah, it won’t be that bad if I carry it on … then I wise up.

The urge to pack your favorite stuff is a strong one; maybe look at those items last during the packing process, not first, and by then you will likely have made them unnecessary through your other, more logically considered choices.

Have any nuts-and-bolts winter packing tricks to add? Let us know in the comments.

Some of Our Favorite Winter Fashion

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Editor’s note: This story was originally published in 2017. It has been updated to reflect the most current information.

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