Many years ago, in the early days of the TSA, just as I stepped through the airport metal detector after removing my belt and watch, I realized I'd forgotten about my cufflinks and tie-pin. Buzzzzzz!
An officious looking gentleman loudly ordered me to go back and send these offending articles through the carry-on bag scanner, then return with my floppy shirt sleeves and necktie askew to face the detector again. I can still recall the incredulous stares of fellow travelers waiting in line behind me, most of whom were stuffed into baggy sweatpants and oversized hoodies. "Look at that fancy-pants jackass," they muttered. "That's the kind of schmuck who buys perfume and a hand-held buttock massager from the SkyMall magazine."
I remember thinking that my satin pocket square probably cost more than their entire outfits. But while I was still fumbling around re-attaching my numerous accessories after security, they commandeered all the convenient seats at the gate, bought the last edible sandwiches in the departure lounge, and drained the sole Starbucks of all its coffee. For all my efforts at Sprezzatura – I was flying to Rome, after all – I was stuck with a slice of stale carrot cake and lukewarm hot chocolate in a styrofoam cup. To add insult to injury, there was even a lonely lump of misshapen marshmallow bobbing around in my drink. At least that's what I hope it was.
The lesson here is obviously: When in Rome do as the Roman do but on your way there just do what the other Americans do.
On my next flight, I sanely decided to wear blue jeans and a crew-neck sweater. Smart casual. But that happened to be the day the shoe removal regulation took effect, and of course my feet were wedged into six eyelet boots that took forever to unlace and wriggle off while everyone else was shod in slippers and flip-flops.
These days I've begrudgingly invested in TSA Pre-approved status. Anything to avoid flying in one-piece romper suit, which is where I fear TSA inspired travel fashion might be heading.