The ultimate seasonless item is an ugly shoe. Every month, one of these foul pieces of footwear—whether bulbous, soleless, or a big-toe coddler—rears its heinous head. Why are we seeking out these busted, demented shoes? I’d like to say it's because we are both perturbed and titillated, which means we are all a bit perverted. Anyway, here’s the latest one…cheers!

A few weeks ago, my former colleague Alexandra Gurvitch clomped through my door in a heinous shoe: the Merrell Jungle Moc Leather Shoe in Midnight. Gurvitch was one of the last great market editors of my era and had an eye for blending high and low in a perverse, spooky way. Here was a shoe she’d no doubt include in one of her pitches. The slip-on shoe has a dopey duckbill shape. The black leather has a slick sheen, as if it has been endlessly buffed. The sole curves deep up into the heel, cutting the shoe in half, while the sole’s rubber tip licks the head of the shoe, ultimately slenderizing the clomper and making it kind of… sexy? Perhaps, ugly-sexy. The dichotomy works. The clunk and the slick! The Merrell Jungle Moc is weirdly… metrosexual! Brawny but manicured. Or like a once-bushy eyebrow that’s been meticulously plucked but still maintains its natural shape.

For Gurvitch, the ugly-sexy shoe has become her go-to when running errands. “I’ve been thinking more about functional footwear and feeling a bit less inclined to wear sneakers,” she tells me. Currently, she’s feeling like “NYC grunge of the '90s, but chic,” she adds. “Walk-my-dog dirtbag, but Prada Sport.”