Who knew men's footwear was so controversial? After the great flip-flop debate of June 2012 we inadvertently stumbled into square-toed shoegate yesterday. Apparently people have very strong feelings about those shoes!

It all started when our friends at GNTLMN told us "As a side note we’ll list the situations in which square-toed shoes are appropriate to wear: 1. Never." And while many commenters agreed, others vehemently begged to differ ("Oh for fuck's sake, what's the problem with square toed shoes for men now?"). The men at Gothamist HQ mirror our commenters on the issue, and we found a similar split response on the streets today:

  • "Square-toed shoes? It's always no. That isn't an opinion. It's a rule."
  • "No. Never. I left Ohio 15 years ago. BUT NOTHING IS WORSE THAN FLIP FLOPS."
  • "I think it just depends on the entire style of the shoe."
  • "It depends how big the square is."
  • "They work. I have a couple myself."
  • "No way, they're terrible. Draws too much attention."
  • "Too classy for me."
  • "I see a lot more of them nowadays, they're okay."
  • "If it's comfortable that is all that matters."

So, we thought we'd try another tack and reached out to one of the most stylish gentlemen we know—Dan Ferrara is a man who makes Don Draper look sloppy. He was firmly against, saying, "Square-toed shoes are for pilgrims and placekickers. The rest of us should stick with the classic shapes. Not too square, not too pointy." He was even willing to give us a reasonable explanation for why:

Style historians like to point to practical reasons for the development of features in men's clothing. For example, vents were added to jackets to relieve the bunching that occurred when a gentleman sat on a horse. Maybe there's a practical reason for the rounded toe as well; maybe it even has something to do with horses. But at this point, would that matter? It's just consensus. As in so many things in men's style—width of lapels on the jacket, width of ties, number of pleats on the pants—there is a flow within a certain range.

As we remain split on the issue—where do you stand?


With Claire Voon and Nina Goldman