Best Travel Clothes For Fall and Winter Excursions

Packing for cool weather is a snap with these lightweight, versatile pieces. Plus: the best travel shoes, bags and accessories!

by | Nov 4, 2022 | Fashion, Travel

best travel clothes for fall and winter. Woman trying to fit stuff into her suitcase

Now that many of us are getting back out there and traveling again, it’s time to revisit our travel wardrobes.

We all know air travel isn’t what it used to be. These days, every flight is full, yet the airplane seats and aisles keep getting smaller. Because it costs extra to check bags, everyone is schlepping a larger carry-on. Which means that if you aren’t lucky enough to have priority boarding, you can’t relax before a flight. Instead, you find yourself standing in a crowd near the gate, planning a strategy to get your suitcase on board and wrangle it into a cramped overhead bin.

Basically, it’s becoming more important than ever to travel light.

I’ve always known a few packing tricks: Choose lightweight and versatile pieces. Roll your clothes, instead of folding them, inside your suitcase to avoid wrinkles. Use a garment cube to corral smaller items like undergarments and T-shirts. For longer trips, bring what you need for up to a week, then handwash items at the hotel. Choose pieces that work together in terms of color and style, so you can mix and match to create multiple outfits.

But here’s what I still find challenging: Finding just the right shoes that will take me from day to night, that will be comfortable enough to walk in for miles, yet stylish enough to wear in shops and restaurants. And finding wardrobe staples that are not only durable and lightweight, but look great. Because who doesn’t want to feel great on a vacation or business trip?

The last few months I’ve been traveling a lot. And doing a lot of research on the best travel clothes, shoes and accessories. The following suggestions include some items I’ve been using myself, as well as recommendations from stylish, globe-trotting women I know. I’ll be adding to this list as I discover more great products in various price points, and if you have suggestions, feel free to DM me on Instagram.

Bottoms

Most pants can be worn more than once during a trip without washing (assuming you’re not doing serious hiking or engaging in major athletic endeavors). Jeans, as you know, can be worn over and over again. I’ve found the key to packing no more than three pieces is making sure the styles and colors work with everything else I’m packing—including my shoes—and that each item serves a unique purpose. For my recent trip to the UK, I packed three pairs of pants in a similar silhouette: wide-legged jeans for both day tripping and casual dinners, wide-legged athletic pants for more active sightseeing, and dressier (but comfy) black flare pants. Because all three bottoms shared the same looser fit, they all looked great with the shoes and tops I brought.

In terms of selecting a pant silhouette for fall and winter, there are a few things to consider. Slim styles (including leggings and skinny jeans) work well with a wide variety of shoes, from boots to sneakers. Straight and bootcut legs are more flattering over mid-calf boots and protect your ankles from the elements. Wide-legged silhouettes are fashionable and flattering, but can be a nightmare in the rain and snow. While cropped looks are cute and versatile, they work better for spring and summer travel—unless you’re vacationing somewhere warm.

More Beautiful’s picks: For lounging on the plane or elsewhere, try some cozy lounge pants, a pair of bootcut athletic pants, or super-soft joggers. If your trip calls for a lot of walking, opt for a wider-cut pant, a pair of quick-drying hiking pants, or some versatile leggings that can be dressed up for evening. If you’re looking for travel-friendly jeans consider a stretchy style with an adjustable hemline, or a fast-drying skinny jean that maintains its shape.

 

Best travel clothes for fall and winter

Tops

When traveling during the cooler months, it’s important to consider both under and outer layers. You’ll need a few long-sleeve, thermoregulating Ts that can be worn alone or under something else, one or two sweaters (or another thicker outer layer, such as a zip-up hoodie), as well as a couple of dresser shirts (such as a button-down) that can be dressed up or down. Make sure everything you pack is in the same family of colors, so the pieces work with one another.

More Beautiful’s picks: When selecting base layers, look for wrinkle resistance and comfort. Focus on materials that wick away sweat and moisture, and are breathable. Merino wool is the gold standard for travel material as it can be both insulating and cooling, and is soft to the touch, wrinkle-resistant and durable. Runners-up include polyester blends, modal, nylon, rayon and tencel. For a sporty look, try a stretchy crew with moisture-wicking and SPF, something soft that comes in a rainbow of colors, or a lightweight option that keeps moisture at bay. For colder weather, a merino-wool style is a practical choice.

In terms of top layers, lightweight pieces in insulated fabrics will keep you warm without taking up much room in your suitcase. Try a versatile sweater in sustainable cashmere, a cashmere-merino shirt jacket, a collared silhouette that looks great over button-downs, a lightweight cable-knit, a cashmere hoodie you’ll wear over everything, a wool crew or a relaxed V-neck. If you prefer to keep your neck covered, opt for a loose-fitting alpaca turtleneck with a stylish open back, a more casual turtleneck, or a budget-friendly pick that comes in several hues. A more casual trip calls for a lightweight vest like this or this in a neutral color.

If you have room in your suitcase and plan to hit up some nicer restaurants or bars, pack a couple of dressier tops, such as a wrinkle-free button-down, a tailored button-down, a T-shirt/button-down hybrid or a sustainable V-neck that can be layered over a button-down.

Dressier Outfits

If you must travel this fall or winter with a dress, make sure it’s a lightweight piece that will pack easily without wrinkling, and basic enough to be worn more than once. You can use jewelry, scarves or jackets to change up the look. And don’t forget to pack some opaque tights to keep your legs warm!

More Beautiful’s picks: Try a universally flattering A-line dress, lightweight jersey dress, or ribbed midi style that can be dressed up or down. A warm yet travel-friendly wrap dress is another great option, along with a crepe shirt dress and (for chillier climes) a turtleneck sweater dress. If you’re traveling for business, consider a stretchy travel blazer or a wear-with-anything sheath.

 

best travel clothes for fall and winter

Footwear

How I envy those of you who can pack one pair of shoes for a week-long trip. I consider the packing a success if I can manage just two: supremely comfortable, weather-resistant shoes that can take me from day to night, as well as a dressier shoe or bootie that’s as stylish as it is comfy. My biggest challenge is that I often need to throw in my running shoes, which take up a lot of valuable suitcase real estate—and, if I’m being honest, I feel frumpy sightseeing in them. Once someone designs a light-as-a-feather running shoe that looks amazing and goes with all my outfits, I’ll be in heaven.

More Beautiful’s picks: This cute, stretchy slip-on sneaker comes as close as I’ve gotten to the perfect pair of travel shoes; it’s comfortable enough to walk around in all day, and it’s more stylish and versatile than a true athletic shoe. Of course, the sock trainer that started the travel-shoe trend was this Balenciaga cult fave, but the price tag is hefty; this Michael Kors knockoff is a solid alternative that I tested myself during a recent trip to New York (with great results). If you’re looking for a day-to-evening style that gives you a little lift (something we petite girls love), try a city moc, lug-sole wedge, or sleek leather bootie that’s easy to break in. If the forecast is chilly, slip-on bootiesfur-lined ankle boots, sherpa-lined water-repellent booties or an insulated, lightweight hiking booties are all good options. If the itinerary includes hiking on rough terrain or an extraordinary amount of walking, consider a waterproof hiking shoe, an all-weather bootie or a classic Chelsea boot that can hold up for miles.  If you’re all about lounging during your trip and/or maximizing comfort on the plane, splurge for a pair of candy-colored, wool-lined booties.

Outerwear

For fall and winter travel, try to hone in on one insulated yet lightweight style that’s roomy enough for you to layer over a shirt and sweater. Extra points: a jacket with a hood!

More Beautiful’s picks: A versatile parka, a fleece-lined jacket or a down-filled style will all glide over multiple layers and keep you cozy. An oversized puffer with a drawstring waist is a flattering pick. A sleek city jacket is a worthy splurge that can be worn year round, while a three-in-one layered jacket gives you options in fickle weather. Looking for a bargain pick for a quick trip somewhere colder than where you live? Try this water-resistant jacket bargain.

best travel clothes for fall and winter

Bags

When I travel, I like to bring one sleek carry-on tote or backpack, as well as a small crossbody purse for walking around at my destination and going out at night. I put my most valuable stuff—cell phone, passport, cash, sunglasses—into the crossbody, which I wrap around my torso while walking around the airport. Then, if I’m also bringing a carry-on suitcase, right before boarding I tuck the purse into the tote bag, which I’ll slide under the seat during the flight. The tote (or backpack, if you prefer) also contains my iPad, chargers and headphones, reading material and/or travel documents, tissues and wipes, water bottle, and a very compact, lightweight travel umbrella. I sometimes put a hat in there too, if I know it will be raining and snowing at my destination, and for longer flights I might tuck in a spare pair of contact lenses. Note: Both bags—the tote and the small crossbody—should coordinate with all my travel outfits.

My perfect carry-on tote is lightweight, has durable straps, and slides easily under the airplane seat in front of you. Obviously, it must also be large enough to house your crossbody bag and other items you plan to bring onto the plane. Bonus points for a tote that has multiple and/or outer compartments, to help you avoid digging for stuff like your headphones and lip balm during a flight. Especially in the dark.

More Beautiful’s picks: When selecting your carry-on tote, look for a lightweight, waterproof and washable bag with roomy compartments. I’ve used this super-light, machine-washable, multi-compartment one for years. I also love this lightweight waterproof classic that takes you anywhere (and its lack of compartments is easily remedied with this nylon purse organizer that slips in and out of most large-size tote bags). If you prefer a backpack, go for a streamlined style with an outer zip pocket, padded shoulders and a laptop compartment (if you’ll be working during your trip). In terms of the small crossbody, I like this one with a cool zipper treatment, this style with a pocket for everything, or a waterproof look with anti-theft technology. A downsized camera bag is fun alternative, while a stylish leather splurge is a worthy investment.

Little Extras

Yes, there are a few more things you should consider packing for fall/winter travel! More Beautiful’s picks: A versatile wrap, wool scarf and/or washable beanie offer additional layers of warmth. A compact travel umbrella protects you from the elements. And don’t forget the travel-sized laundry detergent if you’ll be gone for longer than a week; one packet cleans a sink-full of hand-washables. And because you can’t always be 100 percent sure that familiar suitcase coming down the conveyer belt is yours (even if it’s bright blue), a personalized luggage tag is always a good idea.

Happy Travels!

Listen to Get Away With Your Girlfriends, my fun conversation with travel entrepreneur Lisa Najarian, about organizing fantastic girls weekends and other trips. Lisa and I share our favorite destinations and must-have travel items, and talk about why friendship travel is essential to our wellbeing.

Note: This story contains a few Amazon Affiliate links, which may earn me a tiny commission if you decide to make a purchase.

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