I'm telling you guys, all the women I know love these shoes.

- Scott Schuman, The Sartorialist

In the world of fine men's footwear, the monk strap shoe is somewhat hard to define. It is at once utterly elegant yet utilitarian. And while its origins are forever lost to legends, it's believed the style does, in fact, begin with monks high in the Italian Alps, who fastened their simple leather footwear with a single buckle. The style has since evolved—now two buckles are almost the requisite—and while they are unadorned, the shoe is hardly pedestrian. Traditionalists would appreciate Peal & Co.'s English-made monk strap, but we're partial to this burnished calfskin pair by To Boot New York. Handmade in Italy, the triple-stitched toe cap is not a requirement, but offers a subtle stylish touch. Another touch of in-the-know style? Leaving the top buckle undone.

$395, at Nordstrom