Along the way men transferred their affectations elsewhere—the Great Male Renunciation sloughed off the flamboyant and the jaunty—and convinced themselves of the high heel’s effete connotations, which of course never made any sense. What is the cowboy boot, the preferred footwear of the most masculine caricature conceivable, if not a high-heeled stunner? The conspicuous flash of the cowboy’s heel is insulated by its utility (necessary to keep it in a saddle’s stirrups), but the teetering thrill of a few extra inches is surely undeniable.

Still, something subversive in a men’s heel persists, a gleeful flouting of arbitrarily prescriptive rules, the frisson of something unallowed and untested. Women have recognized the stiletto as a fount of sexualized power for a century. It was only a matter of time before men unyoked themselves. Harry Styles, the spiritual heir to the joys of pop rock’s sartorial swagger, has been dallying about in a selection of Gucci heels (it helps that he’s on the payroll); last month he announced an upcoming world tour with a tightly-cropped image of his shoe’s heel. Marc Jacobs has taken to clomping around New York in a series of Rick Owens vertiginous “KISS” boots, an ankle-high, squared-off Chelsea style in buffed leather with a three-inch stacked platform midsole that ascends, like the build before a log flume drop, into the exclamation point of a four-and-a-half inch block heel. It’s total, uncompromising camp, and pictures of Jacobs in them, vamping downtown, admiring the foliage in Central Park, doing jazz hands, suggests he’s never had more of a ball.

Men find canny ways to skirt gender edicts. For generations of men desperate to carry a bijou handbag but hemmed in by calcified gender codes, liberation arrived in the shape of the harness pack, by all appearances a bum bag but styled as a gun holster, an acceptable concession ratified by every streetwear-addled man under 35. There’s precedence, too, in Dr. Martens, a classic of the genre, a combat boot with a hefty lug midsole and heel to match which, because of its history in the punk scenes of London and New York, carries an unimpeachably hard-edged look. For the more assured pocketbook, Christian Louboutin offers his own take, a polished version with a slightly more pronounced heel that willfully jostles gender norms.