Fun fact #1:
The loafer was originally designed in the 1930s by Norwegian dairy farmers for literally ‘loafing’ around the fields. Americans visiting Europe at the time spotted these comfy classics and started buying up big.

So where does the penny loafer come in?

Fun fact #2:
In 1936, American shoe manufacturer G.H Bass decided to add a split leather strip across the front of the shoe that was designed to look like a pair of lips. This was then further adapted by resourceful school children who used these little pockets to store pennies (for emergency phone calls) and the rest is (preppy) history.

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1. Proenza Schouler penny loafers, $546.51
2. Dieppa Restrepo penny loafers, $396.80
3. Jil Sander penny loafer, $586.80
4. Tod’s penny loafers, $380
5. Tod’s ‘Classic’ penny loafer, $608.51