This site has limited support for your browser. We recommend switching to Edge, Chrome, Safari, or Firefox.


🔥 NEW! An Elevated, Comfy Short for Summer SHOP NOW

🧵Encircled is proudly ethically-made in Toronto, Canada LEARN MORE

👚 Ready to refresh your summer wardrobe? TAKE OUR STYLE QUIZ

3 Comfortable and Cute Airplane Outfits

{This is a guest post by Jessica from The Belle Voyage

Have you ever shown up to the airport in your pajamas?  I totally have.   

Essentials for the Everyday Traveler. Ethically made in Canada with sustainable and eco friendly materials.

For so many years, I thought it was the only way to fly.  I mean – what more could a girl want than to be comfy as could be at 30,000 feet?  

That philosophy lasted until I had to take my very first business trip…with my boss.  I knew that showing up in sweatpants wasn’t going to earn me a promotion anytime soon, so I had to re-think my entire strategy when it came to what I’d be wearing on the plane.

Since that very first work trip, I’ve learned a few tricks to crafting the perfect comfy and cute airplane outfit – no matter what kind of trip I’m taking.   



To me, the perfect airplane outfit should accomplish three things. 

First, it should be an outfit that consists of multiple layers.  My experience with air travel is that planes are either freezing cold or nauseatingly hot – and sometimes both in the same flight!  So an outfit that can adapt is key.

Second, a perfect airplane outfit will incorporate the largest pair of shoes that you plan to bring with you. I try to whittle down which shoes I’m packing to two or three pairs, and then plan to wear my largest ones on the day I fly. By wearing the largest pair that you plan to bring with you, you’ll have lots more space in your suitcase for everything else that you want to pack.

Finally, the best airplane outfits can be worn again during a trip.  Versatility is KEY to being able to pack light – and that means that it’s important to be able to re-purpose your airplane outfit into another outfit that you can wear while you’re traveling. There’s no need to pack something specifically just for the plane!



Warm Weather Getaway

Headed to the beach?  A maxi dress in a comfortable fabric is a great option for the plane. The loose fabric of the dress won’t get in your way, and it’s the perfect foundation piece to layer with a lightweight cardigan. As for shoes, espadrille wedges are a must for any beach vacation, and you’ll save space by wearing them on the plane, and packing a pair of flat sandals.

During your trip, the dress can be re-purposed into a chic dinner outfit, while the cardigan will double as a warm layer for evening beach walks.



Warm Weather Getaway by thebellevoyage featuring black espadrilles



Business Travel

If you’re traveling for work, you’re most likely traveling with colleagues – so the perfect airplane outfit for business travel should strike a balance between comfortable and polished. 

I love to start with black skinny jeans – and I go for ones that are nice and stretchy.  I’ll layer these with a linen t-shirt, and top the shirt with a statement jacket in a neutral color.  Ankle boots finish off the outfit and are easy to slip on and off at airport security.

You can wear the jeans and t-shirt again for casual evening dinners, and the jacket will look great over a sheath dress for meetings.  Statement jackets are great alternatives to a blazer!

Business Travel by thebellevoyage featuring logo tote bags



Red Eye Flight
For overnight flights, comfort is definitely the first priority, especially if you want to try and sleep on the plane.  I’ve moved beyond wearing my pajamas and have graduated every-so-slightly to athleisure wear on overnight flights – which is just as comfortable.

My secret weapons when it comes to overnight flights are legwarmers.  I love that I can take them on and off depending on the temperature of the plane, and they fold easily into my handbag when I’m not wearing them.   Win!

The best part is that all of these pieces can double as workout wear once you arrive at your destination! 

Red Eye Flight by thebellevoyage featuring a nike footwear

Essentials for the Everyday Traveler. Ethically made in Canada with sustainable and eco friendly materials.
Author info

A Midwestern girl turned Southern Californian, Jessica Corson knows how to live life out of a suitcase without foregoing her beauty and fashion favorites.  She has lived and studied on four continents, regularly cross-crosses the U.S. for business, uses her vacation days to embrace new adventures, and always has her travel makeup bag packed and ready to go.  Follow Jessica’s adventures with The Belle Voyage on Instagram, Facebook, Pinterest, and Twitter.

Helpful Links

Leave a comment


Congratulations! Your order qualifies for free shipping You are $225 USD away from free shipping.
No more products available for purchase