Not long after GQ speculated on the possible return of square-toed shoes in 2016, the publication declared the style’s death death in 2017 — but it subsequently included the the controversial toe shape in this roundup of industry insiders’ favorites shoes. The trend has been bemoaned more often than it’s been praised but we’re here to tip the scales in favor of the angular shape that takes the shoe terminology of “toe box” literally.

How Did We Get Here?

Square-toe’s roots go back much further than just Sex and the City. In fact, the shoe shape goes so far back that it’s nigh impossible to trace it to a single place of origin, but it can be seen throughout Japanese history as far back as 300 A.D. in the form of geta, a type of sandal which is made of wood and elevated several inches from the ground via an attached wooden base. Square-toed footwear was donned by Henry VIII and eventually trickled its way down to the laypeople of the time. Chiseled pumps eventually gained popularity in 1960s America thanks in part to Jackie Kennedy — subsequent iterations proliferated in the following decades.

The shoe shape can be seen throughout ’90s pop culture in television, music and movies.

Thanks to fashion’s current fascination with cowboy style, the fact that people still like Friends and the blurring of gender lines, the square-toe has risen in the trend cycle once again. But the tragedies that outfit the feet of the painfully unaware aged suits aren’t the strain of square-toes here. The ones of today are fashion-forward — they find the elusive line between chunky and refined. Or they lean heavy into the chunky shoe aesthetic that’s both elegant and elephantine.

The rise of western wear brought with it satin shirts and fringed suede jackets, but square-toe boots have been lining the shelves of places like Boot Barn for years. Storied boot brand Lucchese has a dedicated lineup of square toes and startup cowboy boot brand Tecovas recently introduced their angled take.

Nostalgia for the ‘90s took hold of the fashion wheel in recent years with many a fashionista gravitating toward Rachel Green-inspired ‘fits while wide-legged trousers dominated trend circles that overlapped workwear brands like Carhartt and Dickies with high-fashion labels like Junya Watanabe and Our Legacy. The shoe shape can be seen throughout ’90s pop culture in television, music and movies. Though not tied only to the ’90s, the recent uptick in Clarks’ Wallabee shoes, one of the few shoe classics with a square toe, have provided an easy mental segue for those looking to dip their toes into a squared-off profile.

As gender norms continue to be challenged, so too does the engendering of clothing face questioning. The square-toe boot has been the bell of the ball for women’s brands like By Far and Ganni and brands like Gucci, Thom Browne and Balenciaga have included square-toe shoes in their collections alongside gender-non-conforming themes. Eckhaus Latta persists in championing gender-fluid ideals and its latest collection (which doesn’t divide its clothing into genders) somehow shoehorned a square-toe out of several pairs of Uggs, which are known for, aside from its cozy fleece lining, a bulbous profile.

Whether or not you’re on board, it’s a shape that will continue to rise and fall in popularity. So if you’re just not ready this time around, maybe you will be ready when it makes its way back.

Diesel Western Boots by Cody James $170

The Jackson by Tecovas $255

Loafer by AE McAteer $385

Comfort Craftsman by R.M. Williams $495

Balans Chelsea Boot by Tiger of Sweden $550

Camion Boots by Our Legacy ~$684

Horsebit Loafers by Gucci $890

Tabi Boot by Maison Margiela $1280
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