A slip-on style shoe, penny loafers are defined by a small detail located on the vamp. Across it, on the top of the shoe you’ll find an additional stylised piece of leather with a small cut-out, which gives the shoe its name. In the ‘40s and '50s American college students took to the style, putting pennies in the cut-out, partly as a way to stand out, but mostly so they had change to pay for phone calls home. Penny loafers were born.

G.H. Bass is heavily linked to the penny loafer - the US brand popularised the style when it brought it to America back in 1936. The design was inspired by traditional Norwegian fisherman’s shoes and, as a nod to this, G.H. Bass called its version the ‘Weejun’ to pay homage to its origins. Initially the American market favoured their Weejuns as house slippers, but it didn’t take long for them to be worn out and about.

It was those penny-wearing Ivy League college students who helped make the style a casual menswear staple, adopting it as their de facto uniform and giving birth to its preppy reputation. American college students continued to rock penny loafers on campus throughout the ‘50s and ‘60s, and were further bolstered by prep-king John F. Kennedy, who too enjoyed them throughout his (most stylish) presidency.

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