From Norwegian day-laborers to preppy college kids, the quintessential penny loafer has come a long way... while mostly remaining exactly the same. It's become an American classic, and true to form, it's one of the easiest shoes in the world to wear — not too fashion-y, not too fussy, and it'll probably look great with 75% of your closet. Ours is handsewn in Portugal — in fact, one hour of hand-stitching goes into each pair — with moccasin construction and a slightly higher vamp for an especially comfortable fit. In black calf, this pair leans a bit more formal than your average pair of handsewns, so it can be dressed up with a suit or dressed down with a pair of jeans.