When it comes to travel, one of the most common questions I get is: what do you wear when you fly? I’m now rethinking my standard answer.

Comfort Or Class? What To Wear When You Fly

I’ve long believed that how you dress matters, even when boarding an airplane. While airlines no longer require a jacket and tie in premium cabins, there’s still something to be said for looking sharp when you fly. It communicates respect for yourself, respect for your fellow passengers, and respect for the privilege of air travel.

At the same time, I realize that by packing passengers in like sardines and cutting service in domestic economy class, there is no luxury in flying any longer…and the price has come down so much that it is a commodity for the masses. $29 tickets in 2025 dollars? When it comes to the cost of air travel, we are in the golden age.

For me, the answer of what to wear is not really dependent on the trip. Whether longhaul or shorthaul, I’ll usually opt for a pair of dark trousers, a collared shirt (though increasingly a t-shirt), and a light blazer. Slip-on shoes are a must for security. If I’m traveling on business, a suit jacket comes with me, but I’ve gone from wearing it to bringing it along in a garment bag.

Sometimes on domestic trips, I will wear polo or t-shirt with clean white sneakers, which (I hope) strike the right balance between comfort and dignity. Even if I’m connecting to a redeye later, I’d rather look put together during the day than shuffle through the airport looking like I just rolled out of bed.

I recognize that people have different priorities. For some, it’s all about maximum comfort and nothing else. I get that, but to me, travel is more enjoyable when you make an effort. You never know who you’ll meet onboard, whether it’s a future business connection, a long-lost friend, or even just a crew member who takes notice and treats you a little bit better. Yeah, I do think you are treated better if you are well-dressed and well-groomed (though forget about the upgrade to first class!).

And one final point: you represent your nation too. I’ve always thought it curious that some passengers board a flight to Europe in flip-flops and tank tops, only to arrive in Paris or Frankfurt and stick out like sore thumbs, screaming, “I’m an American!” Dressing well doesn’t mean dressing uncomfortably. It’s about balance, and in my experience, that balance pays off.

All that said–and the purpose of this story–I’m thinking about making the shift to high-quality athleisure for my travel. As this sort of attire becomes more mainstream, I’m looking for outfits that are high-quality, comfortable, and can be washed over and over again without wearing out, but also look decent. I’m open to hearing any suggestions you may have. Don’t worry, unlike the model above, there will be no midriff showing…

CONCLUSION

So, what do you wear when you fly? For me, it’s about trying to balance comfort with class (recalling that somewhat tragic but undeniable reality from Wicked, “It’s not about aptitude, it’s the way you’re viewed”). I’ll never fault someone for prioritizing comfort, but I continue to argue that air travel is a special occasion worth putting some effort into. How about you?

Any suggestions on new travel outfits for me?

top image: @helenowen / Instagram