Dressing For Business Travel

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Despite its voyeuristic value and surprising staying power, the tale of busty, leggy Kyla Ebbert nearly being tossed off a Southwest Airlines flight this summer for dressing too skimpily (and parlaying it into a pictorial and video feature for Playboy.com) didn’t shed much light on the topic of dressing for the road. Sadly, the delivery of useful information about travel attire is left to bald, fat messengers like me.

So take it from this eternally rumpled flier on the aisle: Edit your wardrobe both to breeze through security and to survive a week or more on the road with a modicum of style. It’s not about dressing down; it’s about whittling down.

Let’s start at the beginning, which is the airport security checkpoint. I always watch in amazement (and annoyance) as travelers continue to wear the wrong things—and too much of them—and then slow themselves and everyone else down.

Six years after 9/11, you’d think travelers would finally get the message: The Transportation Security Administration is serious about its sometimes petty rules of attire. Wear a hat, and a screener will demand you have it scanned separately. Dress in layers, and a screener will make you peel them off. Shoes must be removed, no matter how many laces they have or how many holes are in your socks. Wear metal, and you’ll—ding—be pulled aside and subjected to “secondary screening,” a unique form of public humiliation involving a long wand being shoved near and around your most private parts.

I’ve found that the fastest way through security is to go plastic. I switched the brass buttons on my blue blazer for plastic ones. I bought a plastic Swatch watch specifically for road trips. I’ve even gotten rid of my belt. Needless to say, I wear only slip-on shoes, and I check my socks for holes before I leave home.

I won’t argue that this all sounds a bit unstylish. If you want to don jewelry, sport your favorite chunky metal watch, and wear your lucky running shoes, and if you really need a belt, do what I do: Stow these possessions in your carry-on bag, then put them on once you clear security. And here’s an incredibly useful tip: Stash potentially problematic items in zip-top plastic bags. Before you reach the checkpoint, dump everything—keys, jewelry, pens, handheld computers, cell phones, loose change—into a bag and place it in an exterior pocket of your carry-on. When you escape the clutches of the T.S.A., fish out the zip-top bag and return everything to your person.

The other area of concern about on-the-road dressing is the matter of packing enough clothes to get through a business trip. Or, more specifically, getting through a business trip stylishly.

Here’s the secret to a limited wardrobe: Also limit your color palette. Everything you take should work together. The fewer colors you choose, the more flexibility you have to mix and match outfits. The more you can mix and match, the further you can stylishly stretch your business-travel attire. Personally, I am Mr. Monochromatic on the road. If it isn’t black, blue, white, or gray, I don’t pack it. That’s a rather severe approach, but you get the point.

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