James Bond was no fan of shoelaces. In fact, Ian Fleming informs us in On Her Majesty’s Secret Service, Bond “abhorred” them. My resemblance to the British superspy may begin and end there, but for many years I shared his aversion to those fiddly bits of string, symbols of school, office and deadly routine. No Oxford, however sleek, could tempt me from my chosen path, which I trod in Chelsea boot (winter) or loafer (summer). Sneakers, you ask? Vans slip-ons, thank you.

Then one day, like Paul on the road to Damascus, or in my case Madison Avenue, I underwent a conversion. The color was the first thing that caught my eye, a rich cognac-y brown glinting in the window of a fine old English (if Italian-owned) shoemaker. Next I noticed the distinctive skein of perforated bands decorating the shoe, a solidly constructed number, fore and aft. Here was a lace-up with none of the meek prissiness I associated with the genre. I was sold, instantly if not cheaply—it cost me $695 plus tax to shed a lifelong prejudice.

The shoes in question were of course wingtips, or so Americans call them, on account of the perforated pattern at the toe. On Bond’s sodden shores, they prefer “brogue,” after brog, the Gaelic for shoe. Brogueing, meanwhile, refers to those all-important perforated bands. These were originally meant for drainage, though it might take a scientist or an ancient Scotsman to explain why having holes in your shoes would help keep your feet dry. Today, brogueing is purely decorative, and in a twist of supreme irony, it has recently been applied to all manner of slip-ons, including, in some enterprising if misguided cases, sneakers. Even I can see that this development is wrong. As for 007? I’m confident he would have abhorred it.

Pick up a serious pair of wingtips from Florsheim by Duckie Brown, on sale now on Gilt Man.