The term “square” is most often used to refer to a person who is embarrassingly behind the times: old-fashioned, awkward, dull. As far as insults go, it’s borderline wholesome, reminiscent of a time when girls in poodle skirts and ponytails danced to Bill Haley and the Comets, sipped malted milkshakes and spent dates necking at the local drive-in movie theatre. “Hip to Be Square,” Huey Lewis and the News’s upbeat ode to middle age, chronicles a protagonist’s lifestyle change from self-mythologizing “renegade” to a stable teetotaler who regularly works out and eats healthy. The most poignant moment of the song, besides the noodly sax solo, is when a lesser band member demonstrates his commitment to the square agenda by snapping his fingers and bobbing his head in a perfect approximation of how a fifty-year-old white man might dance at a Rolling Stones revival concert.

lanvin ss20, Bottega Veneta SS20

The origins of the geometric insult are murky at best but go back far enough in history and the verbiage has its distinct roots in style. In A Classical Dictionary of the Vulgar Tongue written by Francis Grose in 1785, an entry for “square toes” reads thusly; “an old man; square-toed shoes were anciently worn in common, and long-retained by old men.” William Makepeace Thackeray’s 1862 novel The Adventures of Philip on his Way in the World, uses “square-toes” to refer to an ancient gentleman who taught himself how to dance. A stick-in-the-mud character called “Professor Squaretoes” appears in an 1887 script published in American humor magazine Puck.

How ironic that the very style informing the English language’s definition of out-of-touch is once again finding favor. Since Y2K, the fashionable consensus on square-toe shoes has been that they’re an egregious abomination of good taste. GQ once penned an op-ed arguing that, like John Tucker, the square-toed shoe “must die.” But the silhouette and its passionate haters appear to have reached a détente.

Versace ss20

A rethinking of the taboo began with the deliciously blunted mary janes shown at Maria Grazia Chiuria’s S/S ’18 collection for Dior and is currently cresting with Balenciaga’s aggressively cleaved pumps and Bottega Venetta’s inexplicably popular duckbill sandals for F/W 2019. (Despite being worn by what feels like every influencer on the planet, Fashionista attributes Bottega’s Venetta’s skyrocketing popularity to hype instead of clever marketing.) The trend does not appear to be abating, with snub-nosed footwear making an appearance on the S/S 2020 runways at Preen, Rochas and Versace, to name a few. Lanvin had thong sandals that resembled Japanese geta and Bottega Veneta continued to flog their now-signature silhouette in the form of stilettos, sandals and woven leather slippers.

The right-angled shape experiencing a current vogue has less in common with fashion’s previous flirtations with geometric silhouettes – Roger Vivier’s buckled flats from the 1960s or 1990s Prada Sport — than it does with the obscene duckbill slippers worn by King Henry VIII as painted by Hans Holbein in 1536. In the portrait, the imposing monarch assumes a broad stance, exaggerated by a wide-shouldered cape and what Elizabeth Semmelhack, senior curator at the Bata Shoe Museum, refers to as “cow mouth shoes.” Though Henry VIII looks every inch the all-powerful monarch, in actuality he was busy executing his second wife and uprooting organize religion, which led to rebellious uprisings and outbreaks of violence during his rule. Perhaps it’s fitting that square toes have returned to an era in which a different broad, flame-haired leader is using petty grievances to wreaking havoc on the population under his control.

Preen SS20, Rochas SS20

According to Jonathan Walford, senior curator of the Fashion History Museum in Cambridge, Ontario, square toes “have a sensible aspect to them. “They’re the anti-fetish. You don’t see too many fetishists who are into low heels and wide toes.” Historically, he says pointed toes have been considered a more elegant silhouette because they elongate the foot and emphasize a narrow shape, whereas square toes make the foot appear wide and indelicate. There’s a pragmatic element to their appeal as well. “Pointed toe shoes get worn out quickly. They stub and get caught on the hemlines of dresses. The square toe is a little more practical,” he says.

Their utilitarian nature may be the answer to the square toe’s current appeal. More and more, fashion is beginning to seem like an impractical flight of fancy. The looming threat of climate change makes the concept of throwing out our wardrobes in service to the creative whims of billionaire luxury companies seem very foolish. The practical option is to hold onto items for longer and wear them until they deteriorate, regardless of fads. There’s a good chance that square toes may outlast their visual welcome this time around, too.