Traveling is simultaneously about planning, then letting go of control. Your flight is delayed? Well, you’ll need to rebook your connecting flight. You can’t get an Uber? Time to look for a taxi stand. Your flight is mid-air and the cabin is freezing and you don’t have a blanket or travel wrap? Well, in my experience taking flights to dozens of countries as a travel editor, that’s a mishap that you can’t really fix in the moment. So don’t suffer, instead, follow my road-tested formula for making one of the versatile, stylish and practical travel outfits I’ve developed.
I'm a Travel Editor and I Swear by These Comfortable Travel Outfits
Double-duty items for the carry-on traveler
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Published Mar 14, 2025
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Clockwise from top: Tracksmith, J.Crew, Everlane, Dana Dickey, J.Crew, Quince, D. Dickey, BR Factory
What Are Travel Outfits?
Travel outfits get you from point A—your home or office—to point B—your vacation or work destination—with maximum comfort and minimal hassle. Stylishness is important, but mostly what you want is to look nondescript and capable. You’re a grown-up, so while you might like to just throw on some sweats like you’re headed to the gym, that’s not going to get you respect from gate agents, which always comes in handy if and when you need help with any scheduling snafus that might happen in the airport. Keep in mind that your travel outfit needs to work in numerous unpredictable micro-climates. Maybe the car to the airport is overly air conditioned, while the taxi that picks you up has no AC at all—and you’ve landed in 98-degree weather. (And you haven’t yet donned your summer travel capsule wardrobe.) Perhaps your seat won’t recline, making your too-snug waistband extra-uncomfortable. Maybe you have to take your shoes off at the security check. Travel outfits need to be thought through so that you can be prepared for pain points.
With these considerations in mind, this set of separates I’m about to share is basically three outfits in one—a tank top and pants, a layered blazer outfit and—when the going gets in-flight frigid—a long-sleeved top and workout leggings under your blazer outfit. Travel can be a sartorial obstacle course but totally doable with these nine pieces. Here’s what to wear and carry on, moving from top to bottom.
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1. Tank Top
I’m not a big fan of wearing tank tops at home, but when I’m traveling, they provide the idea base layer that keeps me warm in lieu of an undershirt, yet can be worn on its own in a stuffy plane cabin or once I reach my tropical destination. I prefer a close-fitting men’s undershirt style or snug cami so that I don’t feel too bulky.
Dana Dickey
2. Button-Front Shirt
Calgary to Mexico, Paris to Sydney, I’ve taken a white or powder blue button-front shirt and worn it on the plane and then throughout the trip. Slightly oversized fit is key, and, psst, spring for the best cotton or linen you can manage, since in my experience, this is a capsule wardrobe piece that you’ll wear again and again, even at home. Layered over your tank top, it’s lovely and warm.
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3. Long-Sleeve T-Shirt
Frequent Flyer Trick, Part 1: Roll up a long-sleeved T-shirt in your carry-on bag in case you need to put it on during the flight. You may not need it, but you’ll feel more relaxed just knowing it’s there, and you can pop it on in the restroom once the plane’s reached cruising altitude. Lately, I’ve been loving technical runner’s long-sleeve shirts for this purpose, since they are engineered to not only absorb sweat but also temperature regulate—and they are so fitted, they don’t add bulk to your silhouette.
Dana Dickey
4. Sleek Jacket
A relaxed blazer in a neutral color is your travel wardrobe MVP, starting with how great it’s going to make you look and feel en route. I swear by my military-inspired blazer in camel. I wear with everything from jeans to dresses once I’m at my destination. And pro tip: sleeves that unbutton so that you can comfortably roll them up are so handy.
Dana Dickey
5. Stretch Pants
Kick flares are the new classic travel pant, surprisingly flattering to most figures even if you never thought a pair of elastic-waist trousers could ever actually work on you. A black or navy pair is the most versatile, as well as forgiving when you’re sitting in airports, cabs and airline seats where who knows what dropped chocolate bars or spilled soda.
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6. Leggings
Frequent Flyer Trick, Part 2: Along with your long-sleeved T-shirt, roll up a pair of leggings in your carry-on bag. These are to put on under your kick flares in case you’re stuck in a terribly cold airplane cabin. I tuck both pieces in a small packing cube and hope I won’t need them, however when I was recently trapped in a freezing cabin on a flight to Mexico, I was so snuggly warm once I put them on.
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7. Socks
I’ve spent more than a little wasted time stranded in airports, looking down at my footwear situation, feeling sorry that I didn’t wear nicer socks. Another bad situation: having chilly feet when I kick off my shoes in flight. Don’t let this happen to you. I like a chunky cotton blend, preferably one that’s thin enough to wear with both running shoes and sandals.
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8. Travel Sneakers
While I love a red Air Jordan almost as much as my teenage son, the mix-and-match styling of a minimalist traveler can’t justify such a loud, sports-specific shoe. I prefer a white or neutral-tone running shoe that is classic enough to wear with everything from shorts to sundresses during my work trip off-hours or vacation sightseeing.
