What Not to Wear

A scene from last year's Not-So-Grand Tour:

On the morning of my departure to Europe, as my neurotic tendencies blossomed with the panic of last-minute preparations, I decided that I absolutely had to have a black dress shirt. Because that's what Europeans wear. Every one of them. Every day. . . . And if I wore a black shirt, I reasoned, I would blend right in. One hundred percent. No question.

So en route to the airport, I stopped at Target, where I pawed through racks and racks of shirts; found one that seemed, at a glance, to fit my diminutive frame; shoved my credit card at a wary cashier; yanked off the price tags; and crammed the synthetic-fiber garment into my bag.

As I put it on for the first time, in Florence, I noticed that it didn’t fit quite as well as I’d hoped, but in the dimly-lit room, it seemed good enough. I would soon figure out, in the harsh gaze of sunlight and passersby, that, in fact, I looked like I was wearing a trash bag. The label may have said “small shirt,” but a more accurate one would have read “two-person tent.”

I also put on, God help me, my nylon travel pants. You know the ones: khaki, nylon, baggy. The sartorial equivalent of an enormous sandwich board reading “Idiot Tourist! Lots of Cash Hidden in the Kinda-But-Not-Really 'Hidden' Pocket—Help Yourself!” Their light weight and multitudinous pockets—including that ostensibly secret one—make them peerless for airplane travel, which is why I bought them, but I have no idea what possessed me to wear them that day in Florence.

And then, suave gent that I am, I finished off the outfit with black socks. I had packed only black socks, in fact, because I had heard that white ones were the classic sign of the American tourist. Shockingly, even in spite of the shirt and the socks, no one seemed to mistake me for an Italian.