The Joy of Being Underdressed

Clothes no longer make the man — as long as both are clean

Jeremy Helligar
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Photo: Andreas Stamm/Getty Images

IfIf 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.

InIn 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.

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Jeremy Helligar
LEVEL
Writer for

Brother Son Husband Friend Loner Minimalist World Traveler. Author of “Is It True What They Say About Black Men?” and “Storms in Africa” https://rb.gy/3mthoj