Winter Travel: How To Pack Light When Clothes Are Heavy

It wasn’t until I began packing for a New Year’s Eve celebration in the Windy City that I realized how much more challenging packing during the winter would be than during the summer. My carry-on suitcase that typically fits nine bathing suits and four pairs of flip flops was now overflowing with one turtleneck sweater and half of a parka. Um, not gonna cut it.

Unless I wanted to be trailing around Chicago under-dressed and ill-prepared, I had to figure out how to roll, squish, squeeze and zip up a winter-approved wardrobe in one tiny suitcase. Here are my tricks for staying warm resourcefully whether you’re gearing up for a trip to Toronto or a destination in Denver.

Stick To Neutrals

Since sweaters don’t need to be washed as often (you’re not sweating in them like you are a tank top on a 90 degree day, at least that’s my logic), you can get by with fewer tops. Stick to neutral colors and use your accessories (see next item) to change up your look. Since you’ll most likely be in and out of museums, shops, and restaurants, chose warm cardigans and a light long sleeve t-shirt so you can layer, and un-layer, as necessary.

Functional Accessories

Scarves are a traveler’s best friend. As a makeshift blanket, a temporary hood or even a pillow, scarves lend themselves to any scenario. Choose a bright color to compliment your neutral wardrobe and, let’s be honest, the drab winter time could use a pop of magenta. I often throw in a vest to add an extra layer of warmth to wear both on the plane and when out and about. And despite the misleading temperatures, don’t forget to pack bring your sunscreen. Protect your body from the frigidness, but also the damaging rays that can still peek through those snow clouds!

Shoes For The Elements

Shoes should be all about functionality. There ain’t nothin’ cute about slipping on unshoveled sidewalks and taking a knee while mid-way across the street. Leave your finest riding boots at home and find a pair with good traction and an appropriate material for warmth and durability. It helps if there are limited laces so you can get through security as quickly, and gracefully, as possible. Remember to pay attention to what’s underneath, too. Heavy socks are ideal, especially wool ones that won’t soak up moisture. I also like to bring my light weight sneakers to slip in a workout if I can find a gym nearby. Wear your boots on the plane to save space and tuck your other shoes into a plastic bag to keep your clothes dry and dirt-free.

All Hail The Leggings

As if you needed reminding that black leggings are the savior of any trip. Not only do they pack well, but the take up limited space and match everything. Take it one step further and make sure yours are fleece-lined and have enough substance to keep you warm. On a really chilly day, wear them under jeans for another coat of warmth.

Tetris Packing

Stuff undergarments into your shoes. Roll pants tightly and tuck socks into open crevices. Wear your bulkiest items and be realistic with what you bring. If you don’t have a fancy event lined up, leave the heels at home. Other than the earrings I wear on a daily basis, I don’t bother to pack any unnecessary jewelry. Make sure you pack your heaviest items (sneakers, thick sweaters, etc.) towards the bottom of your suitcase where the wheels are, it’ll help prevent it from tipping over when upright!

Surprising Supplies

Although you might be dreaming of fluffy flakes and snow covered trees, Mother Nature is not always so kind. It just so happens that I was greeted on New Year’s Day in Chicago with a downpour. Make sure you pack a tiny umbrella to not only protect you from the rain, but to keep you dry in case temperatures reach freezing later on.

Finally, Vaseline, and this is not just the Chapstick addict in me condoning this. Brisk winds and low temperatures can dry out anything exposed to the cool air. Use it to keep lips moist and on dry, cracked hands (I’ve even used it to protect the skin around my eyes when needed).

What’s your go-to winter item?

I wear my infinity scarf non-stop. I’ve used it as a blanket on overly air-conditioned flights and as a face mask when caught in a blizzard (which happens more often that one would think having grown up in upstate New York).