Men in Heights: The Gendered History of Heels

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.

Where once innovation in menswear was marked in glacial increments of suit lapel drift, a man dressing himself in 2019 is spoiled for choice. A lot of this is thanks to the European creep into American taste: if Alessandro Michele’s Medici maximalism at Gucci doesn’t thrill, there’s Demna Gvasali’s Balenciaga’s Central Bloc chic. These are two wildly different expressions of taste and proportion, and yet, each is pushing a men’s block heel: Gucci with horsebit ankle boots, the word “Kitten” hammer-stamped on its two inch stack; Balenciaga with a glossy pretty-ugly square toe trailing a minorly more demure inch-and-a-quarter. You can find a straight flush of two-inch ankle styles in the current crop from Balmain, Lemaire, and Fendi. Y/Project has an especially mesmeric calf-high stack heel in oil slick patent leather. A high-octane treaded pair from Thom Browne, with pin-buckle straps and antiqued gold-tone hardware, looks like Timberlands on HGH, perfect for a morning of Madison Avenue mountaineering. Amiri suggests a suede Jodhpur with silver studded straps that promise the muted sheen of a Robin Hood enjoying early retirement in Palm Springs.

Of course most classic men’s dress shoes have been built with a modest heel for generations, a poorly kept secret that, like the necktie, is a holdover of subconscious masculine assertion. How funny is it that most of the men who would balk at the assumed feminized notion of wearing a heel already do so on a daily basis? To placate them, men’s heels usually exist in angled, stacked proportions that have precedence in the sturdier Cuban heel, so named for the style’s popularity among Flamenco dancers, as opposed to the taper of the stiletto, which apes the idealized feminine shape.

Because of its latter-day verboten status, the heel’s appearance on a man is like a natural wonder, like clocking a meadowlark in a scrum of pigeons. It’s instantly read as provocation regardless of the particulars or total aesthetic effect. This is true of the Tabi boot, Maison Margiela’s split-toe secret handshake introduced in 1988, a fashion deep cut until last year, when Margiela began offering them in men’s sizing, a heretofore inaccessible imprimatur opened to a new swath of men looking for something—anything—else. A picture of Stefano Pilati, late of Yves Saint Laurent and Zenga, attending Pitti Uomo in Florence in 2017 positively bleeds sprezzatura: the designer in a pair of well-worn Tabi boots, leaning against a sun-baked wall, ascending from the cobbles by eight ecstatic centimeters of cylindrical stacked leather, a spent bottle of San Pellegrino at his feet. If there’s a better appeal to men to get lifted, the world hasn’t yet known it.

Max Lakin is a journalist in New York City. His writing has also appeared in T: The New York Times Style Magazine, GARAGE, The New Yorker, and more.