30+ Cute And Comfy Travel Outfits For The Plane, Train, Or Car (2024)

Traveling is composed of different mini-adventures: going to the airport, waiting for the next layover, going to brunches, dinners, field trips, night markets, museums, and more. No matter where you are going on a vacation, you want to make sure that you’re dressed comfortably and are ready to travel.

Two crucial factors that you must remember when you pick outfits for travel are context and appropriation. Some places (e.g synagogues, temples, museums, etc) may require you to dress modestly, so doing a brief research on the place you’re visiting is important.

Comfort is also something you should consider when picking an outfit. When you travel, it’s best to keep it on the comfy and safe side. Wear clothes that you have already worn before or try doing a “dress rehearsal” for your new clothes before your trip so you don’t end up with a piece of clothing that’s uncomfortable once you’re already stuck on a plane. You would want to wear something that you know works.

And, of course, you can’t forget about style. Adding a bit of style and thought into your outfit will not hurt unless you take away the comfort from the equation. Always pick your pieces with both comfort and style present.

I’ll share some of my favorite outfit pieces and outfit combos next. Otherwise, scroll ahead to check out 30+ travel outfits for inspo!

Invest in Basics:

Investing in basics can give you the opportunity to pack light on your trip. Bring a couple of “repeatable” pieces that are not easily spotted. It doesn’t mean that you will be wearing one boring outfit the whole way, it just means packing something versatile and something you can mix and match.

This is particularly important if you’ll be traveling a lot. For example, you might be flying a few different times during your trip and taking a train. You don’t need tons of different outfits just to get from one point to another!

Of course, bring in some trendy pieces to combine with your tidy whities and your sleek blacks.

1. Leggings

Leggings are kind of a travel staple. I literally never get on a plane without them. If you’re on a trip, especially a tour or an airport layover, you would want to keep it flexible but stylish. Instead of a dress, wear a cute but casual top (like a crew neck sweatshirt or sweater) over leggings.

2. White/Black Sneakers

Classic white/black sneakers are a travel must-have. You just can’t go without them, especially on a plane or in a car. A pair of classic white/black sneakers are the epitome of comfort and style. Plus, these sneakers can definitely be used during the rest of your trip.

And besides, tired feet are the ultimate spoilsport. Wearing pretty but uncomfortable shoes may cause blisters, keeping your head out of the fun. A snug pair can keep your feet in the best condition.

3. Classic White Tee

An all-around white tee is another wardrobe (or suitcase in this circ*mstance) must-have. It is as versatile as it can get! Once you’re at your destination, you can wear it with a maxi skirt, tailored pants, shorts, and culottes — the possibilities are endless. Plus, when in doubt, you can always throw on a white tee for your plane ride or road trip.

4. Denim Jacket

No matter the season, a good ol’ denim jacket is the best lifesaver. It is stylish, comfy, and thick — perfect for warming up for a quick nap at the airport. It looks great with black, white, gray, and beige. Pairing it with a floral ensemble is also a good idea as it balances the elements present by adding a classic and neutral show.

5. Lightweight Jacket

Alternatively, you can bring a lightweight jacket to the airport during the summer. The sun may be up and about, but surely, you can’t survive in the airport or the plane with a crop top without catching a bit of a cold. Choose a comfortable but still cute jacket to dress up a pair of leggings.

On the other hand, if you like to keep a light suitcase during colder months, a pocketable down jacket is your best bet.

6. Leather Jacket

A leather jacket is the best alternative to a denim jacket if you’re looking for something thick, stylish, and durable. If your style is edgier, a leather jacket is the best travel companion.

This can also elevate your outfit pretty quickly.

7. Crew Neck Sweatshirt

I’m loving the crew neck sweatshirt right now. It can be layered with so many different outfit pieces (jacket, leggings, etc.) and isso comfy but trendy.

Comfy And Cute Outfit Ideas

Here are my favorite cute and comfy outfit ideas for your road trip, plane ride, or general day of travel.

Denim Jacket + Crop Top + Sweats + White Sneakers

Crop top and sweats? Sloppy. Add in a nice denim jacket and a pair of sneakers? Super stylish. Traveling with comfort and style just takes a little statement piece to stand out!

Black Hoodie + Black Pants + Blazer + Black Sneakers

Want to make an edgy street style appearance as soon as you get to your destination? Adding a little unique twist can make up for it. You’ll be ready to rock the streets when you land.

White Collared Blouse + Knit Sweater + Black Leggings + Black Sneakers

Going on a business trip? You don’t have to wear sweats to stay comfortable during a long trip. Wear a nice knitted sweater over a white collared blouse for a presentable, stylish, and comfy fit. You’ll never have to worry about seeing a client on your flight.

Crop Sweater + High-waist Leggings + Sneakers

Want to keep it simple? You don’t have to make a lot of fuss – especially if you’re rushing about or if you’re just trying to keep it a hundred percent comfy.

Oversized Sweater Dress + Sneakers

Traveling in the cold seasons? An oversized sweater dress and a pair of sneakers can keep you snug and cozy in one go. This is one of my favorite looks for a road trip or train ride during the fall/winter.

Knit Crop Sweater + Black Biker Shorts + White Sneakers

A carefree ensemble. Put on a nice knit crop sweater and a pair of biker shorts so you can move swiftly and freely during long waiting times. I would bet for a Kim Kardashian-inspired ensemble (beige crop sweater + black biker shorts + bulky sneakers).

White Shirt + Ripped Jeans + Jacket on waist + White Sneakers

Don’t know what to wear? Wear what you already have! With an all-around white tee paired with distressed jeans, you can easily come up with a complete stylish fit. For an added accent, you can put on a jacket or sweater on waist that can come in handy when it starts to get cold in-flight.

Black Sports Bra/Crop Top + Leggings + Oversized Coat + Sneakers

Going on a quick trip? A sports bra top underneath a nice oversized coat can give you a chic on-the-go aura – like you’re waiting to get on the next plane for a yoga session in a different city. Love the vibe!

Grey Shirt + Denim Jacket + Black Pants + White Sneakers

You can never go wrong with monochrome. Black pants and a nice loose grey shirt can make a nice outfit for quick coffee trips during a layover. A denim jacket can keep you warm when the A.C. is on high!

Striped B&W Tee + Silk Scarf + White Pants + White Sneakers

Want to travel like a Parisian? A striped tee and a printed silk scarf can give you a classy, chic, and sophisticated aura. Personally, the best outfit to get croissants with.

Vintage Rock Band Tee + Leather Jacket + Washed Denim Pants + Sneakers

If your style is more hipster-like, there’s no reason why you shouldn’t rock a vintage band tee on your trip. The best example of this ensemble would be one of Kendall’s favorite fits. For the jeans, I would prefer to wear distressed black than dyed denim. But it’s all up to you!

White Tee + Black Jeans + Grey or beige Cardigan + Sneakers

Wearing a cardigan is like wearing a blanket. If you’re dreaming of a comfy, cozy trip, you should get invest in a high-quality cardigan.

Where To Buy Comfy Travel Pieces:

Converse

Converse is one of the best cult classic brands out there. Starting out as a basketball shoe, it has grown into a stylish wardrobe must-have. No matter what your personal style is, a pair of Chucks can seamlessly blend into it. Plus, they have a variety of colors to choose from. Personally, I would pick their Black All-Star Chucks, but playing with colors is a fun way to add spark to your outfit.

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Vans

Alternative to the classic All-Star pair, Vans play a healthy competition with Converse. It started out as a skate shoe, eventually growing into a must-have pair in hipster communities. If your style is composed of rock band tees, distressed jeans, plaid — Vans is a good brand to consider.

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Nike

If you have a bit more budget, a pair of classics from Nike is a great addition to your travel fits. My favorite is a pair of white Air Force casual sneakers that I usually pair with neutral ensembles, monochrome outfits, and printed dresses! It is a bit bulkier than a pair from Converse and Vans, but it balances the volume in some of my outfits.

If you’re a sneakerhead, there are a lot of other choices from Nike as well – a pair of Jordans look good with any comfy travel outfit as well.

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American Apparel

American Apparel is good at providing high-quality basics and stylish clothing. A lot of their pieces are inspired by trendy silhouettes, but they are all grounded in versatile and classic elements. Crop tops, skirts, and denim are some of my favorites from them. Plus, they’re a hundred percent American-made!

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Uniqlo

Uniqlo is a home for affordable high-quality, technical, comfy, and stylish pieces. This is the haven for people who are passionate about packing light. Find pocketable down jackets, windbreakers, vests, and Airism (lightweight) technology tees that are guaranteed accessible — no matter your budget.

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H&M

H&M has everything for the trendy traveler. Find rock band tees, distressed tops, cut-out crop tops that look laid-back and fashionable. They also have the best selection of sweaters in my opinion. From knits, crops, cotton, and more!

If you’re a fan of DIY-inspired clothing, you can find a lot of distressed jeans and cut-out shirts from the store. I’ve always loved DIY, but being able to buy clothes that are close to my imaginings always comes in handy. And H&M almost always gets what I have in mind

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Zara

Along with H&M, you can mix up your travel wardrobe with classy and “trendy basics” from Zara. I particularly love their neutral and classy palettes (beige, cream, black, gray). And their coats are always on point!

Click here to shop.

Nordstrom

Nordstrom is home to luxury brands like Marc Jacobs, Balenciaga, Bottega, Veneta, Coach, Burberry, and Jacquemus. I love bringing a small belt bag that can fit my travel needs (passport, ID, wallet, keys, etc) along with a tote where I can fit a book to keep me company but I don’t keep important belongings in a tote where I am most likely to replace. In that way, you don’t end a trip empty-handed.

Click here to shop.

30+ Cute And Comfy Travel Outfits

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