Comfy Airport Outfits And Matching Sets Good For Travel

When it comes to getting through airport travel in 2025, the cliche “it’s about the journey, not the destination,” has never been more true. With all the freaky plane shit (and I’m not talking about the Mile High Club) the media keeps shoving down our throats to make sure we can’t relax in the airport, we might as look chill AF instead. But traveling comfortably and traveling in style are actually one and the same if you look carefully enough. This one is for all my travel girlies girls whether you’re the one type to unironically catch flights instead of feelings, solo travel through your bucket list, or take couples trips as dreamy as the dates on Love Island, this one’s for you. Here’s a shopping guide to the best cute airport outfits for travel. (AKA, how to become the girl people whisper “is that someone famous?” about in the TSA line.)

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Comfortable Matching Set For The Airport

Gap VintageSoft Cropped Logo Hoodie

There’s a reason this look went hard in the 2000s and I’m here to tell you GAP logo pieces are back. These hoodies are made to last for years of comfortable travel to come.

Gap VintageSoft Baggy Wide-Leg Sweatpants

The matching sweatpants complete the look (and will give you plenty of airflow to breeze through the airport).

Luka Belt Bag

Complete the chill cool hottie vibe with the perfect little belt bag (my ultimate TSA hack) to keep you from digging through your carry-on for your go-to items.

Summer Fridays Jet Lag Skin Soothing Hydration Mist

She’s tried and true for a reason and she’ll fit right in your belt bag!

Casual, Chic Sweatsuit For Travel

VintageSoft Wedge Crewneck Sweatshirt

Another timeless option from GAP to keep you cozy, even in the middle seat.

High Rise VintageSoft Boyfriend Joggers

Sometimes you have to run to your connection, and if you do, you’ll want to be suited up in these joggers (that come in so many fun colors).

An Airport Outfit That Isn’t Sweatpants

Anthropologie The Alani Cashmere Mock-Neck Sweater by Pilcro

If you’re one of the brave few who wants to look put together on the plane so you can hit the ground running, combine style and comfort with this sale option from Anthro.

Anthropologie Daily Practice Base Jump Parachute Pants

These pants give Kim Possible in the best way possible, which is coincidentally the attitude you need when dealing with the general public on a travel day.

Best Personal Item Bags

Dagne Dover Landon neoprene Carryall Bag

My all-time favorite, organization-friendly duffle, period. It has a pocket for every one of my problems! Plus, the neoprene is the most pleasing texture.

BÉIS The Crescent Weekender in Berry

The way I need this sleek overnight in the limited edition berry color from Beis… Shay Mitchell, you’ve done it again.

A Sweatsuit That Looks Put Together

Classic Black Sunglasses

These sunnies from Amazon are the first pair I pull from my collection when I travel because they’re classic, cool, and cheap (in case they fall in the ocean or whatever).

Abercrombie YPB neoKNIT V-Neck

It’s a sweatshirt and a sweater at the same damn time. When you buy two, you get 25% off.

Abercrombie YPB neoKNIT Wide Leg Sweatpant

These pants are giving Challengers and who doesn’t want to serve Tashi Donaldson strutting down the aisle? The 25% off applies here too, girl.

Dresses Comfortable Enough To Wear On A Plane

Girlfriend Collective Black Lucia Sleeveless Mini Dress

Yes, this athletic dress is flexible enough to keep you covered on a long ride from point A and point B. Even better, it’s cute AF for drinks when you land.

Athleta Signature Rib Maxi Dress

Layering this (hella discounted!!) dress with a zip-up says I’m a casual queen, but don’t forget the queen part.

Jeans That Look Like Sweatpants

Halara Flex High Waisted Multiple Pockets Baggy Wide Leg Washed Stretchy Knit Casual Jeans

If there’s ever a time to pretend sweatpants are jeans, trying to keep it chic at the airport is definitely it.

Most Comfortable T-Shirts For Travel

Uniqlo Crew Neck T-Shirt

A T-shirt as good as this one elevates a basic outfit to quiet luxury.

Uniqlo AIRism Soft Cropped T-Shirt

Why not add in the long sleeve version for a layering moment?