This story appears in the October 2016 issue of Playboy. Subscribe

Originating on the moors of Scotland and Ireland, the classic brogue has taken on a city-ready footing in a range of smart designer updates this season. This sturdy lace-up gets its name from the distinctive perforations and serrated edges on its surface, called “broguing.” Originally a rough-and-tumble work shoe with open, punched holes, brogues allowed water to drain from the feet as laborers tromped around the bogs. Nowadays the perforations are a nonfunctional detail and often associated with the staid, old-school wingtip. But there’s nothing at all stuffy about this fall’s offerings, ranging from British brand Trickers’ heavy-soled Bourton in a versatile merlot ($645) to iconic designer Thom Browne’s luxury iteration in navy ($1,290). But Jimmy Choo’s Alec (pictured) really caught our eye, with just the right amount of detail and a tonal blue hue that can punch up everything from a slim flannel suit to indigo jeans ($825; all styles at