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The Joy of Being Underdressed

5 min readDec 24, 2019

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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
Jeremy Helligar

Written by Jeremy Helligar

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