An instant classic, whether or not you put pennies in your loafers for luck.

The iconic loafer was born in Wilton, Maine in 1934. Originally made to be worn indoors, they were designed with a distinctive strip of leather across the saddle with a diamond cutout for comfort and durability. First called Weejuns (sounding like Norwegians), they were made by legendary boot maker, G.H.Bass. But when prep school students in the 1950s decided to insert a penny into the diamond shaped slit, the name “penny loafers” stuck and the hand-sewn slip on with the ivy league heritage became ubiquitous for collegiate cool.

Emerging beyond a teenage fixation, the shoes evolved over the years with certain additions like tassels on the front and the introduction in 1966 by Italian designer, Gucci, of a metal horse snaffle bit. Paired with suits by continental businessmen in the 70s and adopted back by Regan-era men, they bordered on becoming a Wall Street uniform, reaching widespread use by the 1980s.

Welcome to the end of the tyranny of high heel. No longer the domain of sockless Italians or Gordon Gekko wannabes, the preppy stable now comes in every fabrication imaginable, including silver, studs and sequins. And as a much-needed alternative to the ballet shoe, a new generation of be-boppers (Elle Fanning for one) has fallen in love with the boy-meets-girl style just in time for fall’s decidedly bookish 70s looks.

Bridget Bardot proving an iconic shoe style is too sexy cool for school.

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