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How to Square Yourself with the Fact that Square-Toed Shoes Are a Thing Again

Generations of haters can stomp all over them, but they’re impossible to kill

Late last month, GQ reported that famed American fashion designer Rick Owens had given Converse’s famous Chuck Taylor high-tops the Rick Owens treatment. In particular, Owens had extended the tongue as well as reconfigured the sole to give the classic sneaker some unexpected flair. But for GQ, it was the “impossible-to-miss square-toe” that really caught its eye. Why? Because in 2017 GQ had tried to permanently expunge the square-toe from the proverbial shoe rack. It was “fucking ugly,” made “your legs look like tree trunks” and had “the power to decimate an otherwise fashionable look.”

Clearly, the magazine capitulated. “The square-toed Chuck Taylor looks like an even more eccentric and punk version of its former self,” it begrudgingly gushed. 

Who could blame the style bible? Even amongst the usually level-headed subscribers of r/MaleFashionAdvice, the square-toe is divisive. “It looks like it should have a little headlight in the front,” a user joked about the Chuck Taylor remix. Yet at the same time, others suggested that while the shape might not be to their liking, they can still understand the appeal. “My friend wore them the other day in white,” one MFA member wrote. “She wore them with some black straight/tiny bit bootleg jeans with a blocky bottom hem. They looked great, but need to be paired correctly.”

It’s an argument that if I’m being dramatic (and why not?) could be said to stretch back to 300 A.D. when Japanese women first donned the stilted geta, the original square-toed footwear. By the 1600s, square-toed shoes — due to the increased roominess — were considered more sensible than their pointed counterparts and were adopted by men too, per The Zoe Report. Then, after several peaks and valleys in popularity, the square-toed shoe reached its apex in the 1990s. First on David Schwimmer’s feet on Friends, and later as the footwear capping off David Beckham’s all-leather-everything look.

These days, their renaissance is seemingly rooted in the so-ugly-it’s-cute vein. For instance, 23-year-old fashion influencer Mark Boutilier tells me that he loves square-toed shoes because they’re “comically long and somewhat clown-like but in the best way possible.” For him, the “hyperbolic silhouette” is what he’s going for since they have a bit of an “uncle vibe.” Moreover, he adds, “They’re accessible at thrifts, which helps more people hop on the trend without having it be a huge investment. It also coexists with the sustainability push.” 

So while Boutilier’s favorite square-toed shoe is by Martin Rose (retail price: $600), you’re sure to find a similar — though slightly less contemporary — pair at your local Goodwill. “Whether we’re looking at oversized 1980s-style suiting, 1970s-style flares paired with a tighter-fitting tee or the square-toed trend, they’re all relatively accessible on the secondhand market,” he explains. 

As for what to wear them with, he does pretty much the same thing as the aforementioned friend of the MFA member: “I have a pair of Eytys Ortega boots that are a take on a Chelsea with a square-toe, and they pair beautifully with wider leg pants. With the surge of wider trousers and baggy denim, it’s only natural for chunkier shoes and sneakers to help even out the proportions.”

What can we say? It’s hip to be square again. 

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