The fugly shoes we’ve walked 10,000 miles in

Long before there was the “freaky shoe” phenomenon and 10,000-step shoe testing on TikTok, there was what we now refer to as the Strategist Fugly Shoe. The Fugly Shoe is the faccia brutta of footwear — orthopedic-y by design but beautiful in its own way. Beloved not just because it looks cool but because it supports your fallen arches and bad ankles.

The first humble pair to grace the site was Merrell Hambleton’s Charleston Shoe Co. Monterey Sandals. “Walk in them. Run in them. Never take a cab again in them — they really do feel like sneakers. You will get compliments on these shoes, and the compliments will be from well-dressed strangers,” she wrote. Apparently, our readers were sold because the South Carolina–based shop later shared that it made $40,000 selling these grannyish sandals on both the Saturday and Sunday after the article appeared.

“I’ll never forget that morning. We all arrived at work only to discover that our website had crashed from an overwhelming amount of traffic,” says Charleston Shoe Co. founder Neely Woodson Powell. “That turned into the biggest day of online sales we’d ever had at that point in our company’s history. We still talk about it all the time.”

One month after came Stephanie Danler’s Danskos. Danler opened her ode thusly: “Two notes about loving ugly things: (1) What is ugly is usually functional, and function is a virtue. (2) You’ll have to repeat that to yourself often because your prettier, richer, more stylish, less functionally minded friends will never stop ridiculing the ugly objects you cherish most.” Danler bought her first pair of Dansko clogs — technically medical shoes initially worn by nurses and doctors before becoming a fixture in professional kitchens — at 15 for a restaurant job, and by now, even Zendaya owns a pair. When I reached out to see if Danler was still a die-hard fan, she told me, “I am not a fair-weather Dansko wearer. The same thing happened with my Tevas, which I have been wearing since high school in Boulder, Colorado. I wore them through the ugly years. Then they were cool again. My fugly shoes and I will live through another few cycles of that.”

There have been many, many more fugly shoes in the years since: Mary-Kate Olsen’s delicately strappy Tevas, Sandy Liang’s bridal Merrells, the Calzuro clogs favored by Italian surgeons, Arcopedico’s woven sock-shoe beloved by both the super-fashionable Misty White Sidell and Portuguese grandmothers.

“I think Strategist readers are, generally speaking, anti-trend. Part of the ethos is testifying on behalf of a product or object that is not cool, per se, but is exceptional,” Danler says. “It gets you off the hamster wheel of Instagram fashion and into cooler, weirder, more personal territory. I don’t care that all the influencer girls are wearing Havaianas. It’s more like, Have you seen Oofos?” —D.P.