11 Pairs Of Loafers—Pennies Optional

In recent years, penny loafers were most often seen on the feet of businessmen dressed for Casual Friday. These days, they’re being worn by the likes of Kelly Osbourne, Kirsten Dunst, and Alexa Chung. This cute-but-nerdy style was a fashion statement in the 1950s, too. Prep school students started slipping pennies into the diamond-shaped slits on their Weejuns (a name shoe company G.H. Bass coined to play on the word “Norwegians” because the style originated in Norway), and the nickname “penny loafers” was born. Not all 11 of these loafers have room for Abe Lincoln’s face, but they’ll all make skinny jeans, short dresses, or mini-skirts look smart.