When it comes to flying, I’ve done it all: long, 30-hour travel days, hoping for some semblance of sleep on red eyes, boarding at midnight, boarding at 6 a.m., economy with about 1 inch of legroom, and business class with all the amenities.
If there’s one thing I’ve learned from logging all those air miles, it’s that not all flights are created equally, and neither are the travel outfits you wear on them. A red-eye calls for cozy, sleep-ready layers, while a tropical landing begs for breezy, resort-ready pieces you can step off the plane and into vacation in. That’s why I’ve rounded up my favorite go-to airplane outfits, each tailored to a different travel scenario, and all of them stylish, practical, and available on Amazon. (And thankfully, a lot of them are on sale right now during Amazon Prime Day.)
For the Long-haul Flight
I’ve been on numerous long-haul flights just this year—according to my Flighty app, it’s 10 this year alone. On these trips, I’ve learned that what you wear can make or break the experience. Enter: the Trendy Queen Lounge Set, a super soft set that is easy to wear without looking like pajamas. I love to wear a short-sleeve shirt on a long-haul flight underneath other layers so I can adjust my outfit depending on the cabin’s temperature. I also love to wear comfortable shoes, like these popular On sneakers, which are light and easy to slip on and off during any security checks or during the flight (I bring my own slippers in my bag just for this purpose).
Any seasoned traveler knows that noise-canceling headphones are a game-changer, especially when you need to sleep on a long flight and want to drown out everything from engine noises to chatty passengers to crying babies. I love these Bose headphones that really do the trick of shutting the world out. And when it comes to a long-haul, compression socks are a must for reducing both swelling and the risk of blood clots. These Laite Hebe ones are cute and do the job, with four zones of compression that help with circulation.
This outfit isn’t just ideal for a long-haul flight—it’s the secret to arriving feeling like you didn’t just cross three (or more) time zones.
For the Red-eye Flight
If you’ve ever tried to catch real sleep on a red-eye, you know it’s an art form—and one that starts with what you’re wearing. The Anrabess 2 Piece Women’s Outfit is the perfect balance of cozy and polished. The soft knit fabric feels like your favorite blanket, but it looks pulled together enough to wear straight off the plane. Like I said, I always pack a pair of slippers, and these Evshine corduroy slippers are easy to put in my personal item so I can slip into them once we’re at cruising altitude; they’re lightweight and fit well with my compression socks. Trust me, your feet will thank you.
To actually get some rest, I swear by a few travel MVPs. The Lunya Sleep Mask is a total must-have and is on rare sale for Prime Day. It’s made from washable silk that feels cool against your skin; in fact, it’s thermoregulating, which means it’ll keep you cool in warm conditions and warm in cool conditions. The mask fully blocks out the harsh cabin lighting and that inevitable sunrise glow before landing. I also love wearing a chic scarf or wrap that doubles as a blanket (after all, even flight attendants recommend against the in-flight blankets and pillows). The Zestt Dreamsoft Travel Scarf is an all-in-one blanket, neck pillow, and shawl, depending on what kind of contortionist sleeping position I end up in. With this combo of items, I can actually get some real rest on a flight.
For the Business Traveler
Business travel demands a wardrobe that’s equal parts functional and polished, because when you’re heading straight from the gate to a meeting, there’s little time for outfit changes. I go for a roomy, wrinkle-resistant pant like these Pretty Garden Women’s Pants; they are structured for a put-together look, but the stretchy waistband and lightweight fabric make them comfortable enough to wear through a long day of flights and Uber rides. Pair them with a ribbed tank top (like this $10 Anrabess Ribbed Tank Top), which layers easily under a blazer, button-down, or cardigan after you land and adds just the right amount of stretch for all-day wear without losing its shape.
For comfy-yet-polished footwear, the Rothy’s Women Slip-on Shoes are sleek, professional, and—bless—machine washable, which means they survive everything from unexpected rain to airport sprints. Plus, they’re made from recycled materials, so a win-win for all. To pull it all together, I love the Oleada Convertible Work Bag, which I use continuously but is quite a splurge at over $600. A more budget-friendly option is this Ecosusi Tote Bag Convertible Backpack that also converts from a tote to a backpack and can hold essentials like your laptop, wallet, keys, and more in its numerous pockets.
For the Comfort-over-everything Traveler
For those of us who unapologetically put comfort first when we travel, this outfit is basically a dream come true. The now-$30 Xieerdo Hoodie Set nails that perfect balance of oversized coziness (who doesn’t love a hoodie when traveling?) and is super soft. You’ll feel even cozier with these Eyean Fuzzy Socks, and the Allbirds Women’s Tree Dashers are feather-light, breathable, and the kind of sneaker you can wear from TSA to the lounge to terminal laps without a second thought.
This Sinaly Travel Backpack is a great personal item as it fits way more than it looks like it should. It’s got pockets for everything—tech, snacks, toiletries—and the waterproof fabric means no panic if you get caught in a downpour or spill your coffee on it. Plus, the padded straps will save your shoulders—it’ll be much more comfortable than a tote or duffel. This entire ensemble is the ideal roll-out-of-bed plane outfit that’ll get you from takeoff to home or hotel.
For the Island Arrival
There’s nothing quite like stepping off the plane and into that first burst of island air—and the right outfit makes all the difference in soaking up that moment. I know people might scoff, but a linen blend pant, like these Faleave Cotton Linen Pants, is the way to do it—and because they’re a blend of cotton and linen, they shouldn’t wrinkle terribly on the flight. I pair them with a button-down, like the Aoudery Button Down, or any relaxed, oversized shirt, as it works perfectly as a beach cover-up or casual topper over a tank or swimsuit that you can take right off.
For footwear, the Oofos Slides are my go-to. They’re ultra-cushioned, waterproof, and honestly feel like walking on marshmallows—plus, they’re easy to slip off when you hit the sand. (Just pair them with socks for the plane, and take them off when you get to your destination.) Keep a pair of sunnies in your bag for easy access when you hit the tarmac, like these Sojos Aviator Sunglasses; they’re trendy without breaking the bank, which is ideal for sandy destinations and the bottom of beach bags.
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