The penny loafer originated in the 1930s inspired by the light, slip-on shoes worn by Norwegian farmers. Popular with both men and women, the easy appeal of the loafer was that it was comfortable as well as smart. The strap on penny loafers was originally a design feature, there to add intrigue to an otherwise simple silhouette. But why are they called penny loafers?

The strap had a small slit was the perfect size to hold a coin, and back in the days when using payphones was the norm, many young men and women would keep money in their shoes in case they needed to make an emergency call.  Years later, preppy Americans adapted their loafers and added silver coinage to their shoes to make a statement. And so, the penny loafer was born.

One of the particular appeals of penny loafers is that they can be worn as both formal and casual wear, for men and women. From high-flying lawyers and accountants to sharply dressed Yale students, the penny loafer has been a style that defies subculture and has truly stood the test of time.

How to wear penny loafers

Penny loafers are an incredibly versatile shoe that can be worn all year round when paired with the right outfit. Follow our top tips to make sure you don’t slip up when wearing these stylish slip-ons:

  • Penny loafers go great with skinny fit jeans or chinos, don’t forget to roll up the ankle to show off your shoes and create a great casual look.
  •  Try wearing penny loafers without socks to create a clean, minimalist silhouette from head to toe
  • Suede penny loafers offer a versatile option that can be dressed up and dressed down for any situation
  • Penny loafers can be worn with suits; pair a light coloured suit with a similar tone of loafer for a great summer look and a dark suit with a patent loafer for a more formal look


H By Hudson Tan Alloa Shoes

H By Hudson Tan Alloa Shoes, £70

These formal tassel penny loafers from H by Hudson offer some serious summer flair. A pair of these is a worthy wardrobe investment.

 Schuh Black Luigi Shoes

Schuh Black Luigi Penny Loafers, £55

A stylish moccasin penny loafer that presents endless styling options. A panny loafer with panache.

H By Hudson Black Chichester Shoes

H By Hudson Black Chichester Penny Loafers, £70

These sharp shoes from H by Hudson are a great price. The traditional shape and attention to detail make them a must-have.