10 Stylish Winter Travel Essentials

Truth be told, winter is one of my favorite and least favorite times to travel. It’s a favorite because it’s festive, and it’s my least favorite because packing for winter trips is a beast. Between the sweaters, jeans, coats, boots, and accessories, I could easily fill my entire sizable carry-on suitcase with one day’s worth of clothes. But since I do enjoy wintertime travel, I’ve done my best to figure out the travel-friendly cold-weather essentials that’ll make life a bit easier (and more stylish, of course). I suppose it’s worth noting that I rarely carry on in the winter and usually check a larger suitcase instead. (If you can carry on in the winter, please tell me your secrets.)

If you have winter trips on your roster, which I’m assuming you do since you’re here, I’m here to offer up some pre-travel shopping and packing advice. Below, I’ve highlighted the 10 items I pack for every winter trip. Take note and feel free to shop items you may be missing, as I’ve included my favorites in each category.

An Oversize Scarf

Don’t worry about this item taking up your in-demand suitcase space. You’ll want to wear it on the plane. An oversize scarf doubles as a blanket in-flight and as a neck warmer outside.

Lightweight Cashmere Sweaters

The beauty of cashmere is that it’s warm but fairly thin, so it’s an excellent sweater option to pack.

Warm Tights

If you want to pack some dressier outfits for dinners and such, skirts or dresses paired with warm tights will take up less luggage space than, say, trousers and a sweater. You can also wear tights under thinner pants for extra warmth, so they do double duty.

Loafers

Loafers take up less space than boots, and especially when paired with socks, they can provide considerable warmth—and they go with everything.

“Packable” Jackets

Certain jackets provide plenty of warmth but miraculously smoosh down to take up minimal space. Free People makes one that I’m particularly fond of.

Long-Sleeve Layering Tees

Layering tees take up zero space, provide extra warmth, and can be worn again and again throughout your trip. My advice is to pack a few—trust me, you’ll wear them.

A Chic Belt

When traveling, it’s smart to stick to basics that you can wear multiple times. Adding in accessories such as a belt will make your outfits feel special.

Medium-Wash Mid-Weight Jeans

It’s best to pack just one or two pairs of jeans when packing for winter. If just one, I suggest a versatile medium-wash pair that’s mid-weight as opposed to bulky heavyweight.

Bold Earrings

When you’re wearing sweaters, coats, and scarves, the best jewelry to wear is a pair of gold earrings that’ll still stand out among all of the fabric.

A Dark-Colored Shoulder Bag

In the winter, I usually opt for shoulder bags that work with coats and sweaters. And when I travel, a dark-colored neutral bag is my go-to so that I only have to pack one bag.