As much of a sartorial staple as a Savile Row suit, the beginnings of the slip-on are believed to originate from the demands of a young Prince Albert of York – later King George VI – who asked London shoemaker Wildsmith to create a comfortable shoe that could be worn at home. It quickly became fashionable among royalty and the landed gentry, rarely appearing outside of stately homes.

In its current guise, the loafer is more akin to the 1930s style of Norwegian shoemaker Nils Gregoriusson Tveranger. Inspired by the moccasins found on Native Americans, his shoes migrated across the Atlantic and found favour with the US market, where it became known as the ‘Aurland shoe.’

In 1934, G. H. Bass made his first version of the loafer which he called ‘Weejuns,’ supposedly a play on the word Norwegian. A distinctive feature of this new design was a strip of leather stitched across the saddle of the shoe, featuring a shaped cutout. They were an immediate hit, with everyone from James Dean to John F. Kennedy sporting a pair.

In 1953, the Italians came along and gave their own take on the slip-on shoe. The result was Guccio Gucci’s iconic Horsebit Loafer, which could be found on the well-heeled soles of the Jet Set. On the year of its 60th anniversary, it remained the only shoe in the permanent collection of the Metropolitan Museum of Art in New York, an honour that it’s held since 1985. And who can forget the 1980s, when the shoe was de rigueur for any self-respecting Wall Street executive.

Today, the loafer retains its inimitable appeal. Our only word of advice? You don’t look as good as you think you do when you wear them sockless with skin-tight trousers.

The Penny

The Tassel

The Kiltie

The Belgian

The Horsebit

The Slipper

The Basket