Back in the day, traveling used to be a special occasion that people dressed up for. These days, anything goes! When you’re waiting at the airport, maybe at a TSA line, you’ll see a lot of people wear everything from maybe a regular business suit all the way to a hoodie with sweatpants.
What Should You Wear To The Airport & Why Should You Do It?
Obviously, dirty sneakers, shirts with holes, and sweatpants are acceptable and if that’s what you want to wear, go for it, however, I like to say luck favors the prepared and if you’re dressed up at the airport, it can still have a number of advantages.
Clothes Send Powerful Signals To Others
Let me start with a story. A few years back, I was on a plane, our business was much smaller and we wanted to extend our credit line. I was dressed well and the guy next to started a conversation and it turned out, he was a manager for my local bank. So when I told him what our plan was and had a hard time getting more credit, he was like “Well, wait a second” and he gave me his email address, I followed up with him and I got an increase for my credit line. My banker was so impressed that he called me for the first time ever and wanted to get together with me for a coffee and he was like “By the way, how did you get your credit line increased?”. So the only reason that whole thing started was because I was well-dressed and trustworthy. If I would have worn a t-shirt with ice cream stains, I probably would have not gotten that offer from the gentleman.
Now the easy thing is because everyone else is so dressed down, you can just get a rather casual ensemble that makes you immediately stand out from the crowd.
Your Luggage May Get Lost
The other reason you want to dress up when you fly is that your luggage can get lost. That happened to me just last year on the way to my best friend’s wedding where I was the best man. If I had not worn a nice pair of pants that would actually fit me, I would not have been able to attend that wedding without looking like a complete douchebag.
Specific Pieces You Can Wear When Traveling
I would say find a compromise between comfort, functionality, and stylishness.
A Comfy Jacket
I always wear a jacket when I travel because I can easily take it off, maybe use it as a blanket, or just have an additional layer to keep me warm because you never know how hot or cold it’s going to be on a plane. I like a very unstructured jacket that is extremely comfortable, no shoulder padding at all, and something that you can just throw into the corner that doesn’t wrinkle easily. Ideally, it has enough pockets because between your passport, your phone, your tickets, and other stuff that you need, you want to have enough storage space.
During the warmer months of the year, I often travel in my Safari jacket which has really big pockets, it’s a nice casual jacket and it just is perfect for traveling because of that. Ideally, you want a jacket that is dark so it doesn’t pick up stains or something with a pattern. Alternatively, I think a navy blazer in a soft material such as cashmere, a cashmere wool blend is ideal.
I try to go with a dress shirt, in this case, I am wearing a button-down collar shirt because it doesn’t require a necktie and it is made out of a fabric that is very hard-wearing. You definitely always want long sleeves but avoid French cuffs because the metal may set off the metal detector, you may have to go through stuff again and it’s just annoying. Another really great option for air travel is a long sleeve polo shirt, specifically, a white one.
Now if I go on a longer trip, I always either wear a tie because my luggage can get lost or I try to wear a bow tie or keep one in my pocket because that can be a lifesaver if I need to go to a more formal occasion later on. I always travel with a pocket square but I skipped the boutonniere because when I fold a jacket and put it somewhere, the flower would likely be squished, however, the pocket square instantly upgrades my outfit and makes me stand out from the rest on the plane. In an ideal world, you skip the belt as well as suspenders and just go with side adjusters, however, that doesn’t always work and so a belt that comes off easily is the best way to go.
If you’re on really long flights, I suggest you invest in a pair of over the calf compression socks because it compresses your veins and makes sure the blood keeps flowing and you don’t end up with a blood clot that might be lethal. That’s especially true if you’re an older gentleman; if you’re younger and you don’t worry about it, I still suggest wearing some nice over the calf socks.
If you’re a watch guy, of course, you want to get a wristwatch. Personally, I try to bring it along in my luggage because I don’t want to take it off, put it back on, it’s just one more step when going through security and I simply try to avoid it. Of course, to me, time is money so I invested in TSA Pre and so I waste as little time as possible waiting at the airport.
Slip-On Leather Shoes
In terms of shoes, of course, I go with leather that matches the belt but in the airport travel case, I usually opt for a loafer. It could either be a penny loafer it could be a Gucci loafer. Alternatively, you can also go with a monk strap shoe but opt for something that comes off easily and quickly so no lace derbys or oxfords.\
Lightweight Pair Of Pants
For pants, I like something that is easily washable so usually, I don’t opt for wool dress pants instead, I go with cotton chinos and khaki because they are very neutral, can be combined with a lot, and they can be easily washed if I stain them along the way. Alternatively, during the warmer months of the year, I really like seersucker because it’s very lightweight, it’s comfortable to travel in yet it doesn’t wrinkle very easily and always looks neat.
In terms of a carry-on, I usually bring a computer bag which also contains my camera and all the stuff I need and if I don’t check luggage, I bring a carry-on with really good wheels that is stable enough so I can put my bag on top of it and just maneuver the airport and the cities I am in very easily.