Updated on January 29th, 2024
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If you have holiday travel plans on the calendar, you’re facing enough stress without having to worry about what to wear while traveling. Once you step out the front door with your bag in hand, your immediate future might involve:
- Travel delays
- Familial conflict about politics
- Someone getting drunk and/or crying
- Awkward interactions with relatives who are close huggers or close talkers
Sadly, the right sartorial essentials won’t get your plane to land on time or soften the extreme edges of your family circle. But with the right set of travel clothes, you can at least feel comfortable and stylish — no matter what happens. Even if your holiday plans devolve into chaos, you’ll look good enough to snap a few selfies along the way. And that’s important, because when things don’t go according to plan, a selfie gives you an excuse to smile.
Read on for a list of the eight essential garments to wear while you’re on the go. They’re easy to find, effortlessly stylish, and oh-so-comfortable.
What to wear while traveling in fall and winter
1. Cozy sweater
A cozy sweater is a must, whether you’re on your way to a cosmopolitan big city or headed out for an epic road trip.
You may find yourself walking the city streets, hopping on and off public transport, or having lunch on the boardwalk. And those things are all way more fun when you’re not constantly readjusting your floaty outerwear. Look for something that’s not too bulky, but substantial enough to stay put on a windy day.
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See details on Amazon
2. T-shirt
Layering is key to dressing for comfortable travel. The day you dress for a cold airplane is the day the plane will sit on the tarmac without A/C for two hours. Be prepared by wearing a comfortable cotton t-shirt underneath your sweater.
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- Semi-fitted, side seamed body
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3. Pull-on pants or leggings
A comfy pair of stretchy pants can be the MVP of your trip. If they fit right, they won’t bunch or pinch even after hours of sitting in a car or airplane. You can also pack multiple pairs in a small bag and they’re ideal for layering under skirts and dresses on cold days.
If you’re opposed to wearing leggings as pants, try a slim fit jogger. Not as tight on your backside, but just as comfortable.
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4. Slouchy beanie
A slouchy knit beanie serves more than one purpose. It keeps your head warm when you’re pumping gas on a cold day, it camouflages greasy roots and bad hair days, and it looks chic in a low-maintenance kind of way.
Opt for a chunky knit and a slouchy style in a neutral color, so you can wear it again and again.
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It’s tough to beat Somaler’s highly rated knit beanie, available on Amazon. Choose from a range of color choices. You can also snag a two-pack at a discount or a beanie-and-infiniti-scarf set.
5. Booties
Tall, clunky boots are tough to transport, especially if you don’t want to wear them en route to your destination. Booties make a sensible alternative because they’re more comfortable and easier to pack. With some creativity, you could even jam them inside a carry-on.
Consider a weatherproof model if you’re headed somewhere other than Hawaii, California, or Florida. You’ll appreciate a waterproof Chelsea boot or a stylish snow boot if you get caught in a storm.
Slip-on Chelsea boots are also convenient in the airport security line.
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- UPPER Full grain waterproof leather
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- 7mm Lug Depth
See details on Amazon
6. Crossbody
No one wants to haul around a clunky bag during vacation. The beauty of a crossbody bag is that you can slip it on and go about your business without a second thought. Going hands-free is just plain convenient, whether you’re fast-walking to your gate at the airport or meandering through local shops and attractions.
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7. Scarf
A scarf is a nice style addition, but it’s also an extra layer that can double as an airplane pillow. And just in case you don’t need it on the plane, choose one that’s small enough to shove inside your carry-on.
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8. Packable jacket
Weather is unpredictable. But stashing a full coat in your weekender bag usually leaves room for nothing else. The solution? Try a packable puffer, which brings the warmth without the bulk.
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See details on Amazon
What to wear while traveling: Other considerations
When choosing your perfect on-the-go travel outfit, keep these tips in mind:
- Opt for supportive and easy-to-remove shoes.
- Choose natural fabrics like cotton. They’re more breathable which feels better on longer journeys.
- Skip the embellishments. Metal on your shoes, clothes, or belt can set off the metal detector in the airport.
- Pockets are practical, but you want your stuff in zippable pockets. Don’t buy the sweater with big hip pockets if you’ll be tempted to use those pockets for cash or anything valuable.
- Choose socks carefully. Opt for lighter socks so you don’t get overheated. You can rely on layers and a beanie to keep you warm instead. Compression socks can be great for long plane rides.
For more inspiration on what to wear while traveling, see my post about celebrity airport style.