Square-toe shoes have a special distinction. Hopeful statements that begin with “On the right guy, in the right scenario . . .” do not apply to them the way they do to red-flag items like leather vests and string ties. Nor does any rhetoric about the changeable winds of fashion: “Hey, if acid-wash jeans can make a comeback . . .” Their image cannot be rehabilitated. They’re like Michael Bolton: They will never, ever be cool-ified.

“I don’t think square-toe shoes ever had a good moment,” says New York designer and store owner Steven Alan. “They’re like PT Cruisers.”

That amusing analogy is actually quite profound; in it lies the best—the only—explanation for the shoes’ cockroachlike resistance to eradication. The men who whistle while they tie their shiny black Governor Bradford lace-ups every morning are a lot like PT Cruiser drivers: They’re not stubbornly clinging to an unstylish accessory, they think what they’re putting on looks good.

This cheerful self-delusion continues in the face of evidence to the contrary that’s harder to ignore than anti-smoking ads.

“Square-toe shoes came around in the late eighties and early nineties,” says Enrique Corbi, co-founder of the Belgian shoe label N.D.C. He is mystified by the refusal of some men to let go of the Boyz II Men–era relics. “They went out of fashion quickly. The only places you see them now are cheap chains like Aldo.”

Unfortunately, you see them other places. You see them at the office, on the guy rallying the troops for an Amstel Light–soaked happy hour. You see them on the sidewalks in front of clubs that serve tantric-tinis, worn with black “nighttime” pants and untucked collared shirts.

“I’m imagining that what goes on in these guys’ heads is that they think round wing tips are ‘stuffy’ and square-toe shoes are ‘casual,’” Alan says. “You can see the face of the guy who wears that shoe. He thinks he’s tough. He’s the type of guy who would talk about how he just picked up some girl and she’s in love with him.”

That may seem a uniquely American portrait of unattractiveness, but things aren’t much better across the Atlantic. Corbi says the square-toe-shoe guy is as common in London and Barcelona as he is in New York and L.A.

“Tasteless guys wear them,” he says. “They don’t even go to nice clubs. They go to cheap clubs. Every population has the same segments. We have the trendy individuals, the average individuals, and the tasteless individuals.”

And maybe that’s the reason square-toe shoes have followed us so far into the 21st century. They are the footwear of the hopeless. Someone will eventually bitch-slap the flouncy adopter of style affectations like handlebar mustaches and porkpie hats. The square-toe-shoe guy? Till now he’s just been silently judged inferior, left to march the streets, confident and oblivious. But perhaps it’s time for a charitable wakeup call: Unless you can live with the knowledge that people are wearing your signature shoe to “nineties” parties, invest in a nice pair of wing tips.