The Joy of Being Underdressed
Clothes no longer make the man — as long as both are clean
If I could turn back time and change three things, I know exactly what they’d be. First, I would have come out sooner — probably during the summer between my freshman and sophomore years at the University of Florida. (Though “why then” is a story for another piece entirely.) Secondly, I would have cared less about what others thought about me. And finally, I would have reconsidered my entire approach to footwear.
In my twenties, ill-conceived shoe choice was one of my worst enemies, and I now have the shabby feet to show for it. My insistence on wearing the most fabulous shoes I could squeeze my hooves into — especially boots that were very much not made for walking — left me with a few unsightly souvenirs on my bunioned left foot.
My ridiculous sartorial rules didn’t apply only to me: I refused to look twice at any guy who wore sneakers when he wasn’t running. It didn’t matter what he was wearing on the rest of his body; his feet had to be perfectly attired.
One ex dumped me because he wanted ‘a T-shirt and jeans kind of guy.’ I wonder what he would have thought of Casual Weekend Jeremy.
That’s not to say I was a suited-up kind of twentysomething. I’ve never been one, and, thank God, work has never required me to wear a tie. But I had my own dress code, which emphasized stylish over formal, banned running shoes, and required shirts to be tucked in at all times. Before I finally caved in my early thirties and bought a pair at an Armani store in Milan, I didn’t even wear jeans. I stuck to that code even when I was off the clock. One of the best compliments I ever received came from a model in New York who said I looked like I just stepped off a runway (as she admired a white-on-cream outfit I’d bought on holiday in London).
That’s not to say my rules came without sacrifices. One ex dumped me because he wanted “a T-shirt and jeans kind of guy.” (I guess he wasn’t a fan of the creased black dress pants and tuxedo shirt I wore on our last date.) I wonder what he would have thought of “Casual Weekend Jeremy,” my alter ego, who started emerging every so often in the…