Square-toed
Some feel the shoes are unattractive and unfashionable (they've been likened to Pilgrim's shoes), but fans insist the shoes are more comfortable.
And when respected retailers continue to sell the footwear, it's easy to see why men are confused.
We asked four leading style experts for their opinions about square-toed shoes.
The verdict? A resounding "no."
"I think it's great for people with square feet or people named Frankenstein. Other than that, I try not to think of square-toed shoes," said Scott Schuman, the author of popular style blog The Sartorialist.
Jake Davis, a photographer and director known for his personal style, said the shoes are "generally a sign of a douche, Wall Street type with no sense of style."
"I do understand some corporate environments have dress codes but there are plenty of stylish options out there to avoid the notorious square toe," Davis told us.
Marcus Troy, who offers style advice to thousands of men on his Twitter and blog, cited some of the more comfortable options.
"Advancements in footwear design have bridged that gap between function and fashion beautifully," Troy told us. "Brands like Cole Haan have amalgamated Nike Lunar outsole technology with brogues, wingtips, chukkas, and saddle shoes, making them more awesome than ever before."
But Matthew Rubinger, style expert and director of luxury accessories at Heritage Auctions, told us that fans of the shoes can hold out hope they'll come back in style.
"I personally would never wear square-toed shoes, which were popular 15 to 20 years ago, and aren’t anymore," Rubinger said. "But, who knows? Maybe they’ll come back, double-breasted suits did!"