Stylish And Comfy Airport Outfits | What To Wear On A Plane & What NOT To Wear

I used to think dressing for the airport was simple… until I made just about every mistake in the book.

👖 Too-tight jeans on a long-haul flight? Been there.

🥶 Freezing midair because I didn’t bring enough layers? Yep.

🥿 Shoes that felt comfy until I had to sprint to my gate? Never again.

After years of full-time travel, I’ve cracked the code on the perfect comfy airport outfits.

The ones that keep you feeling good from check-in to touchdown. Today, I’m spilling everything I’ve learned, including what to wear, what not to wear (seriously, don’t make my mistakes), and how to put together effortless travel outfits using pieces you already own.

Let’s make sure your next travel day is as smooth *and stylish* as possible! ✈️

Ready? Let’s get to some cute AND comfy airport outfits!

Article originally shared in October 2023 – Updated in February 2025.

Estimated reading time: 15 minutes

_{*This post contains affiliate links. Which means if you shop for certain things by clicking the links in this blog post, I receive a small commission at no extra cost to you! Thanks in advance for supporting Ways of Style!}

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What to wear on a plane + comfy airport outfits ✈️

– Comfy pants, sweatpants or joggers (a comfortable bottom piece is KEY!)

I recommend straight or skinny so you don’t have to worry about it when you go to the bathroom. I explained this before. This is the kind of pants I love traveling with:

This website has very cute comfy pants!! :) And they are ethically made and very comfortable. (Same brand where I got the pants on the left photo)

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👉🏻 A chic crossbody bag and a travel document pouch are a must as well. This is the one I have :)

👉🏻 I also just got this 20′ carry-on bag, and I am OBSESSED!! 🤩 (use code WAYSOFTHEWORLD for 10% off!)

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– Sneakers or very comfortable shoes:

I’m always wearing sneakers! Any type of sneakers will work here. It’s just nice to travel with comfy shoes and my style of choice is sneakers 95% of the time. You can also wear really comfy flats or sandals, just make sure to pack an extra pair of socks.

This is my favorite pair of sustainable white sneakers (they are the best and not too crazy expensive!). This is the exact link to the ones I have.

Also read: How to wear white sneakers all year round!

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Learn how to pack light! Watch me do it for a recent trip ⬇️

🧳 My Exact Packing Process Video – (How I do it from start to finish)

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– A denim jacket or long cardigan:

It’s smart to travel with an extra layer. Airports and airplanes are kind of unpredictable when it comes to temperature, so it’s always good to be safe. I’m someone who’s always cold. So for me, this is a must! I usually carry a denim jacket or a long cardigan.

As you can see, I’m wearing all my favorite basic pieces for a travel day here: Long cardigan, white T-shirt, leggings and white sneakers. It was very comfortable to travel like this!

PS: best and softest long cardigans here!

– T-shirts:

They are easy to style and comfortable. T-shirts are KEY to create comfy airport outfits! I usually wear a white, striped or black T-shirt. It’s just so easy.

🎯 Browse some cute, affordable and comfy T-shirts here.

– Leggings:

Leggings are great for traveling! I love wearing them for the airport, but also as a back up for working out or use them as pants. As long as it’s not Summer and the temperature is below 65, I’m happy to wear my Spanx leggings anywhere.

Here are some easy outfit ideas to put together for the airport. Pair them with comfy shoes, a T-shirt and a long cardigan or a hoodie and you are good to go.

Also read: Spanx leggings review and ‘What to wear with leather leggings‘

– Dresses or Skirts (midi or maxi):

I recommend longer skirts or dresses because, as I mentioned earlier, you don’t want your beautiful legs to touch those nasty airport/airplane seats.

I have never traveled with a midi skirt until very recently and I found it to be very comfortable. I created a monochromatic look with sneakers and a denim jacket and honestly, it’s been one of my favorite travel outfits to date!

And this is the type of dress I’m referring too. If you are super girly and want to wear a dress on a travel day, of course you can do it while still being comfortable for traveling. Here are 2 midi dresses that I have styled with sneakers. Just make sure to bring an extra layer if you are someone who gets cold.

This is a very easy way to create stylish and comfy airport outfits if dresses are your thing :)

Pro tip: make sure it’s a dress you will also wear during your trip! Don’t overpack ok!?

Unlock Your Perfect Packing Strategy in Just 2 Quick Questions!

Packing should be easy, but somehow it always turns into a struggle…

Too much? Not enough? The wrong pieces?

If you’ve ever second-guessed your suitcase, I have a super quick way to check if you’re on the right track. Just answer these 2 easy questions about your trip, and I’ll send you a customized packing list perfect for any spring or summer trip. Get started ⬇️

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What Not to Wear for a Travel Day – Learn from My Mistakes!

Before we continue with more cute and comfy comfy airport outfits, let’s talk about what not to wear… and more importantly, why.

Some of these mistakes I’ve learned the hard way after years of full-time travel, while others are things I see at airports all the time. Some may seem obvious, but trust me, a few might surprise you.

Now, let’s get into the full list of what not to wear on a plane and why:

1️⃣ Heels:

This one is personal preference, but every time I see someone in sky-high heels at the airport, I can’t help but wonder… why? Sure, they might look great, but they’re definitely not more comfortable than a pair of sneakers or slip-on sandals. And if you have to rush to catch a flight? Forget it.

2️⃣ Jumpsuits:

Have you ever tried going to the bathroom when you’re wearing a jumpsuit? Exactly. Not fun, especially in a cramped airplane lavatory. Skip the jumpsuit unless you enjoy the full strip-down experience mid-flight. This piece is great for traveling, but it stays inside your suitcase.

3️⃣ No Socks:

I don’t know if it’s just me, but walking barefoot through security gives me the ick. It never smells great, and those floors? Let’s not think too hard about what’s on them. If you’re wearing sandals or slip-ons, at least keep a pair of socks in your handbag for the security line. Your feet will thank you.

4️⃣ Belts or Too Much Jewelry:

Going through security is already annoying, so don’t make it harder on yourself. Removing a belt, multiple bracelets, rings, or layered necklaces while juggling your laptop and toiletries isn’t exactly stress-free. Keep it simple and save the accessories for after you land.

5️⃣ Over-the-Knee Boots or Difficult-to-Remove Shoes:

OTK boots are cute, but they’re a hassle at security. Unless you have to wear them because they don’t fit in your suitcase (totally understandable if you’re headed somewhere cold), opt for shoes that are easy to slip on and off.

6️⃣ Too Many Layers:

Yes, layers are great for travel, but too many can turn into a hassle. If you start overheating mid-flight, where are you going to put your extra sweaters and jackets? Unless you have space in your bag, keep it simple with a cozy cardigan, denim jacket or a pashmina that you can easily take off and store.

7️⃣ White Denim:

White jeans, white pants… why would you do this to yourself on a travel day? Between airport seats, tray tables, and unexpected spills, wearing white is practically inviting disaster. If you’re determined to wear them, just know you’re taking a big risk.

8️⃣ Super Short Shorts or Mini Skirts:

Think about it: do you really want your bare legs touching those airplane seats?

I’ve seen all kinds of nasty things on those seats girl. I’ll leave it at that.

9️⃣ Wide Leg Pants:

They’re stylish and comfortable, but they’re also a nightmare when you need to use the bathroom. Picture this: you’re in an airport restroom, pulling your pants down, and the hem touches the floor. Now, consider that airport and airplane bathrooms aren’t exactly the cleanest places (and that wet floor? It’s not water).

Unless you’re willing to roll them up to your thighs every time (which is totally valid, I’ve done it), leave your wide-leg pants in your suitcase.

🎯 Pro-tip: Avoid packing pieces you’ll never actually wear on your trip. That bulky athleisure set? If it’s just taking up space in your suitcase and won’t make an appearance at your destination, skip it.

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What To Wear On A Plane – More Comfy Airport Outfits!

⭐️BONUS: Comfy Airport Outfits If Traveling Somewhere Cold

I struggle when flying from somewhere warm to somewhere cold. This happens to me a couple of times a year at least, when traveling from Florida to Chicago in the Winter to see my family. Y

ou don’t want to be too warm because you’ll be a sweaty mess in less than 30 seconds, but you also don’t want to travel too light because you will die 30 seconds after crossing the exit sign at your destination’s airport.

So, what to do?

Well, these are some outfits I’ve tried in the past. I sometimes have to wear a hat because I don’t like to pack those in my suitcase. Also, traveling with booties can be pretty comfortable too, so I don’t mind them on travel days.

My advice is to keep in mind how you are getting to and from the airport. If you are taking public transportation where it’s cold, then you will have to bring your Winter coat (sorry!).

Other random things to keep in mind when deciding what to wear on a plane:

• Sometimes you’ll have no choice but to wear a hat (sometimes they don’t pack well and you really want to bring them)

• Remember that it’s always nice to bring an extra pair of socks if you’re wearing sandals. You don’t want to walk barefoot where other people are doing the same (ahem security line). And they are nice to have in the airplane too.

• Do you have your period? If the answer is yes, then wear black pants. You never know if you’ll have access to change on time or if you are just running around to catch your flight, end up having no time and the airplane is stucked at the gate, you can’t get up for whatever reason, etc. Things happen, better be safe.

• Do you usually get cold? Bring an extra layer or pashmina.

• What’s the weather like where you are? What’s the weather like where you are going?

• How are you getting to and from the airport? Will you need an extra layer for walking to take public transportation?

• If you have a carry-on bag, make sure to put all your toiletries in a clear bag. We bought these ones and they’ve been life savers at the busy security check-ins.

Things to survive a long haul flight:

• Noise canceling headphones
• Earplugs (if you don’t have headphones)
• Phone charger and travel adapter
• A kindle :)
• An extra layer in case it gets cold
• This face balm OR this fancy face serum (I use both!)

I don’t think you need to bring many extra things. Most airlines will provide you with a pillow and a blanket. We recently traveled with Turkish Airlines and we got a cute goodie bag with earplugs, eye mask, moisturizer and even socks! (and no, it wasn’t business class).

👉🏻 If you’re heading on a long travel day soon, read this post for more tips!

🎯 If you want to never think about packing again, get my ‘Pack Like A Pro’ bundle – you’ll get immediate access to 17 packing lists + resources for just $17!

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Other Posts You May Also Like:

• Joggers VS Jeans – Which ones should you travel with?
• 15 Common Airport Mistakes To Avoid!
• Minimalist Packing Guide – This is what I packed for 6 months of travel! (in a carry-on)
• The Best Shoes I’ve EVER Traveled With! 👟
• How To Actually Pack Less Things!

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Final Thoughts About What To Wear On A Plane:

Dressing for travel shouldn’t be a guessing game. With the right comfy airport outfit, you’ll breeze through security, stay cozy in-flight, and step off the plane looking (and feeling) amazing. No more outfit regrets, bathroom mishaps, or wishing you’d worn something else!

So next time you’re packing for a trip, remember: comfort is key, layers are your best friend, and wide-leg pants? Well… proceed with caution. 😉

Now, tell me; what’s your go-to airport outfit? Drop a comment below, and let’s swap travel style tips!

Safe travels and happy packing! ✨

XO,

Aimara

PS: get your customized carry-on packing list just by answering these 2 questions about your trip.

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ABOUT THE AUTHOR:

Hi, my name is Aimara and I am the voice behind Ways of Style. I was born and raised in Venezuela until the age of 27 when I moved to Chicago, and 2 years later I met my best friend and husband. We now travel full time and live out of a carry-on bag, so believe me, I know a thing or two about how to maximize every single piece I own. 

I love creating new looks, and looking cute while I’m traveling. And in this blog, I try to share all my looks, even if I don’t have the best photos ;) My goal is to help you maximize every piece you have in your closet and to encourage you to live with less things.

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Did you learn how to create some comfy airport outfits for your next trip? Share it on Pinterest!

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• 13 most forgotten travel items
• How to survive long travel days
• 15 best travel essentials for women
• Everything you need to know about personal items
• How to simplify your toiletry bag

_{*This post contains affiliate links as I am a part of Amazon’s affiliate program which means I receive a commission if you shop for anything at no extra cost to you.}