Ask the MB: Are Square-Toed Shoes Back in Style Now?

Q: It's been awhile since you guys have talked about classic black shoes to go with any classic suit. Do you guys still subscribe to the semi-rounded Kenneth Cole oxford, or has a decade brought the square toe back?
—Jordan

A: As you imply, it's been nearly a decade since we last addressed this issue. Specifically, in 2008 we created a Shoe Toe Pointiness Chart. While the shoes we were wearing then are long gone, the advice we dispensed remains sound. Indeed, whenever we are moved to produce a chart, it's usually because we are expressing a law that is based in some timeless geometric or mathematical principle of style. Just as gravity persists, so does the aesthetic appeal of a semi-rounded shoe.

Now to the second half of your question: Just because we're right about the correct shape of an oxford doesn't mean society always shares our opinion. And square-toed shoes have been so out of favor, so long, that in an era that celebrates nostalgic reappropriation and contrarianism, they seem like a shoe-in for a renaissance. And yet we still suspect the odds of that happening are only slightly higher than Tiger Woods winning another major anytime soon.

Kenneth Cole's "Bro-Tenial Leather Oxford"

Why? Frankly, we can't recall exactly why square-toed oxfords had their moment in the 1990s in the first place, but our off-the-cuff hypothesis is that their gimmicky novelty was the source of their appeal. Most shoes were rounded or pointed — so square-toed shoes, and by extension, their wearers — were mavericks! Rebels, Macarena-ing to the beat of a different drummer.

But here's the thing: Who wants to present himself as a guy who thinks his best strategy involves steering as much attention as he can to his feet?

Even Kenneth Cole, who pioneered the square-toed vogue, eventually abandoned ship. His site currently shows 280 shoe styles, and only about six — or 2% — qualify as square-toed. And even they are mostly denatured and relatively streamlined descendents of the ubiquitous right-angled clunkers of Cole's heyday, the New York Oxford. Perhaps the one exception is Cole's "Bro-Tential Leather Oxford," which is exactly as awful as its name warns and unsurprisingly marked down from $118 to $79.