Square-Toe Shoes Stage Their High Fashion Comeback

Way back in 2017, the editors of GQ made their opinions on square-toe shoes painfully clear: They were a geometric disgrace, and they must die. Here’s the thing, though—the shoes we were talking about then deserved every bit of scorn sent their way. They were clunky and outdated, the preserve of sleazy car insurance salesmen and junior politicos from Iowa. It would take a concentrated effort from the buzziest design gods on the planet to make us see them any other way—and six years later, that’s exactly what’s happened.

In 2023, luxury powerhouses like Prada and Marni, along with zeitgeist-y labels like Martine Rose and Our Legacy, have resuscitated the silhouette for a freakier generation of menswear fans, transforming the hapless silhouette into a righteous flex. Angular, squared-off toe boxes are on the runway, on the shelves at the swerviest boutique in your neighborhood, and on the feet of globe-trotting street style stars who couldn’t place Iowa on a map. (With all due respect to our friends in Iowa.)

The key difference? The new breed of square-toe shoes aren’t so square: They’re gently rounded, or slightly pointed, or equipped with so much glitzy hardware they’d make Liberace blush. The 11 options we cherry-picked below aren’t just square for the sheer novelty of it—they’re designed to sync up with everything you should be wearing this fall, from brash striped shirts to cropped leather jackets to nubby double-breasted blazers. Much like John Tucker, square-toe shoes have proven surprisingly tricky to kill. This time around, it might be wise to hold off on the memorial service.