Command Respect from the TSA: How to dress while traveling

by Barron Cuadro  |  in Style Tips

Hey Gents,

As you already know, the way you present yourself is important. It’s your statement; without speaking, you’re telling the world what you think of yourself and how others should perceive you.

Because of this, dressing well should extend to every part of your life. Even at the gym. Even when traveling.

Especially when traveling.

Why? Well, for plenty of reasons, but mostly because it’s your chance to shine.

Sadly, air travel used to be regarded with more respect and reverence. Just look at the photo above. It was an event; people dressed up when traveling.

Nowadays, it looks like a runway show for oversized sweatshirts and cheap pajama pants. And the sad thing is, no one bats an eye, because practically everyone else is dressed just as schlubby.

But not you, dear EG reader. You, my friend, are different. You don’t succumb to the ways of the masses, in their ratty sweatsuits and pajama pants. You know that dressing well is all about presentation and confidence.

Plus, you’re trying to get a bit of respect from those irritable TSA officers.

Here are a few quick pointers on how to dress while traveling.

(Disclaimer: If you take a pro-sweats stance, I’m not interested in hearing your rebuttal, and this site probably isn’t for you in the first place. If you’re thinking, “But I just want to be comfortable! Waaaa!” Suck it up, be a man, and sacrifice a small bit of your comfort to look presentable.)

What to wear up in the air

After jet setting a bit more than usual the past couple years, I’ve finally formulated the perfect travel outfit.

By the way, “perfect” in this case is relative. If you’re looking to command respect from the TSA and your fellow travelers, this outfit is perfect. If you’re hoping to look like a baggy grey mess in your oversized sweats, this will not be perfect (for you).

The Perfect Travel Outfit: How To Dress While Traveling, Effortless Gent

(If you’re reading this on EG, click the image to enlarge, and feel free to share with you friends)

In case this isn’t obvious, you don’t have to wear THIS EXACT outfit. Rather, I’m suggesting some sort of variation of this outfit. Don’t over-think it.

1.) Cotton sport shirt or oxford cloth button down. If I’m going somewhere tropical, I would wear a linen sport shirt, or maybe a polo shirt. The shirt pictured is from Fifth&Brannan.

2.) Lightweight chinos. These seem more comfortable than denim. Choose your favorite color. I typically go with a charcoal or light olive. The ones pictured are Dockers Alpha Khaki. If I’m going somewhere tropical, I’d go with a light khaki color, or some other brightly-colored chino.

3.) Lightweight navy sport coat. The pièce de résistance, if you will. Super comfortable, and takes your whole outfit up three notches. I just bought this one from Uniqlo (also pictured above), and I can already tell it will be my favorite warm weather / travel sport coat.

4.) Shoes. Wear your heaviest shoes, typically your leather lace-ups or loafers. The ones pictured above are Cole Haan (via Zappos). That way, your outfit is complete and you don’t have to lug around a bulky, heavy pair of shoes in your bag.

A quick tip

Always bring a sport coat, and wear it on the plane. You may be meeting with friends, or going out to a nice dinner at some point. You can make use of it, trust me.

I used to pack my sport coat, but the last trip I took, I ended up wearing it. I’ll never go back.

I suggest this method because 1.) you don’t have to worry about excessive wrinkles that come from packing a jacket, and 2.) you look damn good in a sport coat.

Dressing well should extend to every part of your life… Even when traveling. (click to tweet)

Same goes for the suit you were about to stuff in your carry-on. Instead of packing it, just wear it on the plane. Feel free to ditch the tie (or, heck, wear it for extra points).

People have this misconception that suits are uncomfortable, or that you need to fly in frumpy sleeping attire or baggy gym sweats to be comfortable. I don’t subscribe to that at all, and if you’re an EG reader, you shouldn’t either.

How to avoid wrinkling

In case you’re worried about wrinkling your suit jacket while sitting for a few hours, you have a few options.

You can take it off, fold it, and stow it away in the overhead bin. Alternatively, if you have a small bag underneath the seat in front of you, you can lay it right on top.

A third option would be to ask the flight attendant to hang it for you in the closet area up front, but I haven’t tried this one yet. If you’re sitting in First Class, up toward the front, or in the very back, this would probably be more of a possibility.

In reality though, it doesn’t really matter. When you take your first shower at your destination, simply hang up your jacket in the bathroom, and the steam should help loosen the wrinkles.

If you have a linen jacket like mine, the wrinkles add character, so I definitely wouldn’t worry about it.

Other considerations

The airport is often a hot mess. You, my friend, shouldn’t be. Keep in mind these easy-to-follow tips when traveling.

Go lean

Let the lean wardrobe mentality extend to your packing as well. If you’ll be gone only a week, you can fit everything in one carry-on bag. It’s just a matter of practicing minimalism and taking only the necessities.

Prepare to get frisky

You know how the TSA makes you take off practically all your clothing before walking through the metal detectors? Be prepared and do it all before you reach the conveyor belt.

Don’t actually take off your clothing, but if possible, throw your wallet, phone, jewelry, belt, etc. in your carry-on, and be prepared to take off your shoes and jacket.

Don’t wait to do everything until after you throw your bag on the conveyor. You don’t want to be that guy flailing all over the place while the line grows behind you, and the person that was in front of you is already through the metal detector and grabbing his bags.

I always hate Flailing Guy. I’m sure everyone else does too. Don’t be him!

Barefoot? Please.

Wear socks. Unless you don’t care about going barefoot in line.

Oh what, you’re wearing flip flops? Bad move, buddy. Flip flops are for the beach, the pool, or your walks to and from the beach or pool. Wear appropriate shoes next time. Tsk tsk.

Further reading

Here’s another take on stylish and travel-appropriate outfits, from Antonio / Real Men Real Style via Art of Manliness.

A quick update on my attempt at packing light

Hawaii Packing Revisited

A few articles ago, I discussed packing lightly for my upcoming trip. I’m proof that the whole Lean Wardrobe philosophy, even when extended to packing, is a constant work in progress, something that needs practice.

It’s not always easy to predict exactly what you’ll need during a trip. Inevitably there will be some inefficiencies, and you’ll wish you brought more T-shirts… something like that.

All you can really do is take a long look at what you plan on bringing—lay it all out on the bed—and evaluate it.

Think about what you’ll be doing on your trip, and see if your plans align with the clothing you have laid out. Hopefully your selections are activity-appropriate.

My specific situation was a little tricky. I was heading to a tropical locale, but I was also attending a few meetings. I didn’t want to wear T-shirts and flip flops to these meetings, so I had to bring a few dressier options as well.

Specific observations

Turns out that I ended up dressing up in non-beach clothes more often than I thought I would, so I would’ve benefitted from one or two more sport shirts or polos. I didn’t hit the beach that much, unfortunately, so I could’ve survived with one pair of trunks.

I didn’t wear the Chucks much, but I did wear the dub monks, driving loafers, and sport coat a lot. So to those who said I wasted space by bringing them, I laugh smugly in your face.

Just kidding. But, seriously, I did wear them a lot, so you were totally wrong. 🙂

I didn’t wear the red chinos as much as I thought I would; I guess I wasn’t in the mood for brightly-colored chinos. I would have benefitted from a second pair of chinos, maybe ones that were slightly less colorful. Who knows though, moods change and maybe next time I’ll be into them.

Again, packing light takes practice! Even I’m not perfect at it. But, I know for a fact that the more you practice, the better you’ll be. I once was terrible, and I’d bring multiple options for multiple situations, and come home not touching two-thirds of the stuff I brought with me.

One thing I can say is that packing light definitely feels great, just like owning less and having a lean closet feels great. I personally hate lugging around multiple bags, and I never check in my suitcase. If you’re like me, you’ll benefit from the Lean Wardrobe philosophy.

Hope that helps

Where are you headed this summer? Any fun trips planned? Let’s hear it below.

One last thing! A small announcement

Have you checked out Dressing Like a Grownup? It’s the ultimate resource for the younger gent trying to dress better on a small budget.

You can pick up DLAG for only $7, but for a short time, if you pick up The Effortless Guide to Graduating your Style (my first eGuide), you can get DLAG for free. More details here.


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