34 Cozy and Elegant Winter Travel Outfits That Are Worthy of a First Class Upgrade

Airports are like runways of travel styles. You’ve got the fashionistas, the business class pros, the head-to-toe sweatsuit folks, and of course, the infamous flip-flop guy (you know the one). Personally, I’m all about striking a balance. I want to be comfy but still wear an outfit that looks put together with items I can wear throughout my trip. And with the holidays coming up, plus all the winter travel plans on the horizon, I bet your suitcase could use some zhuzhing up with new, cozy travel outfits.

As a shopping writer, I spend a lot of time hunting down pieces that are perfect for everyday wardrobes and any travel lover’s closet. Lucky for you, I’ve done the digging, and if you keep scrolling, you’ll get a peek at the items already on my wish list (and soon to be on yours, too). With picks from some of my favorite luxe retailers like Net-A-Porter, Revolve, Ssense, and Saks Fifth Avenue, these clothing and shoe finds are bound to become your winter travel staples — and, who knows, might even get you upgraded to first class.

Best Travel Tops 

When it comes to picking the perfect travel top, whether you need layers for the plane, stylish shirts for sightseeing, or a gift someone will actually wear, a good rule of thumb is to choose something versatile with odes to your (or your giftee’s) personal style. For example, the Saks Fifth Avenue One-shoulder Cashmere Sweater is an ideal choice for a date night or festive gathering, while the Arch4 Ribbed Cashmere Turtleneck pairs beautifully with a maxi skirt, trousers, or jeans, offering a cozy-chic look for the holidays.

Skims Soft-smoothing Long-sleeve T-shirt

I’m a longtime Skims fan, and once you try on this long-sleeve tee, you’ll understand why. It’s the ultimate airplane shirt, especially in colder months, as it’s cozy, warm, and layers effortlessly. You can style it with jeans, sneakers, and a puffer coat for a casual travel outfit or matching leggings for an easy athleisure look.

Elie Tahari Cashmere Whipstitch Sweater

This cashmere sweater, with its fashionable black stitched details, is an absolute showstopper. Anyone would be thrilled to unwrap this as a gift. It’s perfect for holiday celebrations or the office, effortlessly keeping you looking polished when paired with black trousers and accessories.

Best Travel Pants

Choosing the right pants for travel is key, not just for comfort during transit but to ensure they’ll have multiple styling opportunities on your trip. Below, I’ve found pants that look great and feel even better while offering mix-and-match potential. The Row’s Woolworth Stretch Ponte Leggings are a wardrobe essential if you’re flying, sightseeing, or simply running errands, and the Koa Brushed Stretch Cotton Sweatpants are so soft you’ll never want to take them off.

The Row Koa Brushed Sweatpants

For those who live in cozy clothes, these sweatpants make the perfect gift. Here, dreamy comfort takes style to the max — without anyone ever knowing you’re wearing sweats.

Rag & Bone Miramar Sofie Pants

These Rag & Bone sweatpants are going viral because they offer the look of jeans with the comfort of sweats. If you like looking polished while staying comfortable on the go, these pants are a must-have.

Favorite Daughter The Favorite Pants

A best-seller at Revolve, these Favorite Daughter tailored pants would pair seamlessly with a turtleneck and kitten heels for the holidays and easily transition into your workwear and travel wardrobes when needed.

Best Midi and Maxi Skirts 

I’m a big fan of midi and maxi skirts because they’re an obvious go-to for mixing things up when you don’t feel like wearing pants, and they work across all seasons. If you’re packing for a tropical getaway or dressing for the holidays with boots and a sweater, the Veronica Beard Maxine Wool-Blend Maxi Skirt is sophisticated and timeless. But the Maria Cher Madero Alice Abstract Maxi Skirt, on the other hand, adds a playful pop of color to your winter wardrobe.

Kobi Halperin Femi Cashmere Rib-knit Midi Skirt

This cashmere skirt is a winter must-have with its cozy rib-knit design that’s equal parts elegant and cozy. Plus, it’s currently on sale, helping you save $149 — what’s not to love?

Alice + Olivia Asymmetric Pleated Skirt

Another sale steal, the Alice + Olivia Pleated Skirt is 40 percent off and will be a year-round wardrobe MVP. It’s incredibly flattering, made from high-quality materials, and comes in a beautiful hue that works for any season.

Best Cozy Layers and Jackets 

As a travel shopping writer, few things excite me more than jacket shopping. Investing in high-quality, stylish, and functional outerwear is essential, and I’ve found timeless options that will keep you warm and fashionable on any cold-weather trip — starting with the Moncler Moka Long Down Puffer Coat, which is as sleek as it gets and can match effortlessly with any outfit. However, the Mercer Collective Alexa Belted Trench Coat is a chef’s kiss for layering in fall, spring, or mild winter days.

Sam. Denver Sherpa Jacket

The Sam. Sherpa coat will be your new winter go-to thanks to its trendy two-tone design and cozy warmth. Available in four neutral shades, it’s an outerwear choice you can’t go wrong with since each one is elegant and versatile.

Toteme Quilted Jacket

The Toteme Quilted Jacket is so chic because you can wear it on its own in milder weather or layer it under a heavier coat when it’s freezing. Plus, the quilted fabric is so on-trend and will bring subtle texture to your suitcase favorites for extra intrigue. 

Best Comfortable Shoes

Shoes, shoes, shoes. In my opinion, you really can’t have too many comfortable pairs, especially if you’re a frequent traveler. I’ve rounded up some top picks that are both supportive while still fashionable enough to put the finishing touches on your travel outfits. From the trendy Sam Edelman Elaina Loafers to the comfy Asics Gel-NYC Sneaker and the Stuart Weitzman Belted Leather Boots for a night out, these finds cover all shoe departments and occasions. 

Sorel Joan Now Waterproof Chelsea Boots

The Sorel Chelsea Boots are a classic choice, guaranteed to keep your feet warm and dry while adding a sophisticated touch to any look. They’re built to last season after season, making them a solid investment.

Nike V2K Running Sneakers

I spotted these sneakers and instantly knew I had to have them. They’re perfect for long walks, whether you’re traveling or just strolling around the city, and will become your go-tos in no time.

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