More daring than a Derby and less formal than an Oxford, the monk strap is a versatile dress shoe that pairs just as well with a bespoke suit as it does a blazer and jeans. Characterized by its distinct lack of laces, the monk strap opts for a simple strap-and-buckle design (single-buckle, double-buckle and even triple-buckle varieties abound) which typically can be tightened or loosened over the tongue of the shoe by adjusting one or more notches.
Legend has it that the monk-strap shoe descends from the footwear of European monks, whose sandals and closed-toe work shoes boasted the iconic strap-and-buckle fixture. Centuries later, the monk strap has become a powerful accessory in fashion and popular culture—even James Bond wears monk-strap shoes in the movies, looking stylish as he saves the world from terrorist threats. Quite the trajectory for a shoe of such humble origins—but simple design speaks to the instincts of timeless style, and the monk-strap shoe is decidedly here to stay.
Supposing you're not a secret agent, monk-strap shoes still look best with a suit or dressed down with jeans or chinos (try rolling your pant cuff one or two turns up in the summer, with or without socks).
The greatest strength of the monk strap is its adaptability, and different styles of monk are better suited to individual taste and preference. Hugo Boss (bottom left, $425) offers an edgier, more modern take on the monk with a double-buckle shoe in black with textured vamp. Cole Haan (middle left, $260) delivers a handsome double monk with broguing around the quarters and toe in slightly two-tone brown. For a sleek, understated look, consider the J.M. Weston (top, $895) single monk strap in black.
The black double monk from Kenneth Cole (top right, $195) boasts a classic toe cap, and finally, for those seeking an air of elegance, try the French calfskin pair from Stefano Bemer (bottom right, $1,500), luxuriously tanned a deep-red sangria and touting a single monk strap made from sharkskin.