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How to Stay Warm (and Stylish!) Throughout Your Winter Vacation

Grace Lower | Dec 21, 2020

stylist winter

When I was a kid, I had an inexplicable aversion to winter clothing. For some reason, I equated comfort to frumpiness, so I’d often leave home without a warm hat or a proper coat. Until recently, I thought I’d outgrown that habit—that is, until I spent the better part of winter abroad.

Throughout my travels, I was determined to “fit in with the locals.” I’d notice an effortlessly glamorous group of young professionals and immediately feel insecure about my pom-pom hat and clunky winter boots. For a while, I tried donning my less-practical (but objectively cooler-looking) clothing. After a few frigid walks, I realized that it was far better to be comfortable than stylish…but why not both?

According to an old German saying, “there is no such thing as bad weather, only inappropriate clothing.” After a bit of trial and error (and a lot of people-watching), I’ve found that you don’t have to sacrifice style for comfort when you travel. Here are a few cold-weather must-haves that will keep you feeling warm and looking sharp all winter long.


Accessorize Wisely

1. Slouchy Beanies

A warm, loose-fitting beanie offers a perfect balance of comfort and style, whether you’re hiking or window-shopping. That said, make sure to choose one with a thick knit or a fleece lining; there’s nothing worse than cold ears when you’re on the go!


2. Knitted Headbands

While headbands tend to be more popular among female travelers, there’s a lot to be said about their practicality. The beauty of a headband is that it’ll protect your head and ears without giving you hat-hair.


3. Infinity or Blanket Scarves

Colorful scarves are a must-have when the skies turn gray. Not only do they keep your face and neck warm, but they can also double as a makeshift pillow on a long plane or bus ride.


4. Slim-fit, phone-friendly gloves

Although thick gloves tend to be slightly warmer, slim-fit gloves offer the dexterity needed to find train tickets in a crowded wallet or to look up directions on a phone. For a more polished look, try sticking with neutral colors and materials like leather and fleece.



Layer it on!


1. Thermal Tops

One of the best ways to stay warm is to keep your core well-insulated. Dry-fit, thermal shirts aren’t exclusively for athletes—and they make a fantastic base for layering of any kind.


2. Button-down shirts

Chambray and flannel button-downs are one of my favorite travel staples. While they may not be as warm as a hoodie, they look a bit more polished and work perfectly under a sweater or a crew-neck sweatshirt.


3. Cardigans

Cardigans aren’t just for Mr. Rogers or your local librarian. They combine the comfort of a sweater with the ease of a sweatshirt for quick and effortless layering. Whether you opt for lightweight cotton or cable-knit wool, stick with a fit that’s slim, but not tight—you’ll want to have save room for layers, above and beneath!


4. Waterproof Jacket or Coat

Take a few minutes to research the coldest destination that you plan to visit. Is it typically rainy? Snowy? Windy and dry? From there, choose a coat that’s best suited for the climate. I try to stick with neutral-colored, waterproof options that can double as a raincoat—saving valuable room in my suitcase.


Get a Leg Up

1. Long underwear and leggings

When it’s cold outside, one layer of pants sometimes doesn’t cut it. Pack a few pairs of long underwear or leggings for layering under your favorite jeans. I especially like fleece-lined leggings, since they tend to be even cozier than their cotton counterparts.


2. Dark jeans

It might go without saying, but dark jeans are a travel staple. They’re durable, easy to dress up or down, and can survive several wears without being washed or ironed.


Keep your Feet Feeling Sweet

1. Quality socks

When you’re on the road, a dry pair of socks is your best friend. While thick wool socks are a great option, I tend to prefer synthetic: they wick moisture better than cotton, and they tend to be more breathable than wool.


2. Water-resistant Boots

Even if you aren’t planning to trek through the snow, there’s nothing worse than wet feet. You’ll want to invest in a pair of versatile boots—ideally ones with thick soles and deep treads—to put some distance between your feet and the elements.

While many of my friends love their L.L. Bean Boots, I’ve found that Bare Traps, The North Face, Franco Sarto, and Steve Madden offer practical-but-stylish options, perfect for exploring any city.


Small Stuff

1. Hand warmers

If you’ll be spending time outdoors this winter, hand warmers will be a godsend. I like to pop a few in my coat pockets to make icy walking tours and long waits at the bus stop a little bit cozier.


2. Lip Balm and Lotion

Cold weather is miserable enough without dry skin and cracked lips. To stay comfortable, try to keep lip balm (I’m partial to Burt’s Bees) and a travel-sized lotion on hand.


3. Thermoses

As an avid runner, I’m a huge believer in hydration. While I love my trusty water bottle, a stylish travel thermos can make even the chilliest walk more bearable. Fill it up with coffee or tea for a warm drink (and a needed boost of caffeine) on the go!

While winter weather can be cold and bleak, there’s no reason for you to follow suit. No matter where you travel this winter, remember that it’s possible to pack smart, look sharp, and stay cozy, regardless of the weather. 

About the Author

Grace Lower

Grace Lower is a recent college graduate with a love for writing and an incurable case of wanderlust. When she's not exploring new places, Grace enjoys teaching English as a Second Language, making terrible puns, and running incredibly long distances at incredibly slow speeds.

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