Travel In Style: How To Dress For The Airport

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A polo under a blazer is stylish and comfortable.

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Invest in a stylish carry-on.

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Your luggage should complement your style.

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The Frank Clegg Troy duffle is my leather duffle of choice.

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Wear a pair of slip on shoes. Loafers are always a good choice. A softer shoe like a Tod's Gommino for long flights and something with more structure if you please for shorter ones.

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Unless you've got a Panama hat you can roll safely, keep it on your head even though it's a faux pas to wear a hat indoors. At least it won't look like someone sat on it for the rest of your trip.

What to wear to the airport when you’re going on summer vacation

As a veteran traveler, I’ve learned a thing or two over the years about how to pack and how to best navigate the airport in style. If you’ve been to the airport recently, you know that style doesn’t seem to be the first thing on your fellow traveler’s minds. But that doesn’t mean you shouldn’t look your best and be comfortable and efficient at the same time. Here are a few of my favorite how to dress for the airport tips.

what to wear to airport men

Wear a jacket. No matter how good you are at folding a jacket in your suitcase or carry-on, it’s going to come out wrinkled. There’s just no way around it. So it’s always best to wear your jacket to the airport. If you’re only bringing one, your wrinkle problem is solved. If you’re bringing two, well just make sure you pack a little travel steamer. When you get on the plane, take off your jacket, fold it lightly and store on top of your carry-on in the overhead bin.

what to wear to airport men

| WEARING | Suitsupply blazer, J.Crew polo shirt, Ring Jacket pants, Garrett Leight sunglasses, Homero Ortega hat, Drake’s pocket square, Frank Clegg bag, Shoes c/o Allen Edmonds | PHOTOGRAPHY | by Rob McIver Photo

Taking a hat? Keep it on. Although you shouldn’t wear a hat indoors, we can make an exception when it comes to the airport, because you’re definitely going to want to bring a Panama hat on summer vacation. Unless you own an extremely high-quality hat that you can safely roll up in your suitcase, don’t try to jam it in there. You’ll only be disappointed when you take it out and it looks like it’s been sat on.

Invest in a stylish carry-on. Luggage is practical. Yes. But so is clothing and we put a lot of effort into how we dress. You should put the same effort into your carry-on luggage. Whether it’s a stylish roller or a leather duffle, save up for a bag or suitcase that complements your style. I’ve been in love with my Frank Clegg duffle since I received it this past spring.

what to wear to airport men

Always wear a loafer. Since most times you’ve got to take your shoes off, it’s always best to wear one you can get on and off easily. I always wear some sort of loafer. If it’s a cross-country or transatlantic flight, I usually go with a softer shoe, like a Tod’s driver (the City Gommino is best for the walking you’ll do in the airport). For shorter flights, I’ll wear something with more structure.

what to wear to airport men

Thanks for reading.

Stylishly Yours,

Brian Sacawa
He Spoke Style


Chime In

  • Forrest Howe

    Re: Panama hats and folding a myth. My highest quality Panama I would never consider abusing it like that. After a couple of folds they look sit upon. When traveling I wear a Panama that’s nice looking, not cheap looking, place it under seat in front after doors are closed. If something untoward would happen to it I’m not set back too much.

  • Khoi | Gentleman Within

    3 simple, solid travel tips.


    Problem with attractive luggage is it attracts some of those working the airport who might be somewhat confused as to the niceties of property ownership.

  • Peter

    Amazing post! I am a frequent airport user and always love to use light clothes when traveling. For the shoes I always choose loafers as they are light and easy to take off when required! Just found this spanish brand called Boonper! Im totally in love with their stylish driver shoes! They are so comfortable, beautiful and compared with those of Tods really cheap! Panama hat is also just so chic…

  • Travel ji

    Panama hats are never out of fashion, this look rocks. A comfortable and elegant look for airport travelers.


  • Marcus Paul

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  • I am not sure I would go sockless though…The last couple of times I have gone through airport security, I have been asked to remove my shoes and walk through scanners ect so I think I would prefer to wear socks. With that in mind, I would probably for go the loafers and switch to traditional 4 hole suede desert boots instead…They would not quite have the convenience of the loafers, but would still be fairly easy to take off and put on ect…

  • Lydia Grace

    The carryon bag is to die for, such a beautiful chocolate leather. I agree that you should invest in a leather carry on piece, it will tie in nicely with your outfit when on-the-go, I use the Ebony Black Leather Duffle by MAHI Leather