Punk, sculptural and oversized aren’t exactly terms you’d associate with the penny loafer. Yet, these descriptions best describe how one classic footwear style that we’ve borrowed from the menswear department has evolved with the times.
But first, a brief history: It’s said that the slip-on style was first designed in 1926 as a custom order for King George VI who wanted a pair of casual kicks to “loaf” around in his country estate. The loafer became a fashion hit among rakish gents when the style went into mass production.

Loafers seen at Loewe, Versace and Tod’s for Fall/Winter 2021.
Flash forward to Fall/Winter 2021, and you’ll find that new-gen loafer today boasts more flamboyant updates and plenty of hybrid styles. At Prada for example, the loafer’s traditional upper gets melded with chunkier creeper soles to give the look an air of punk subversion. Meanwhile, at Loewe, the loafer gets a massive transformation with thick sculptural soles that give it an almost sneaker-like appearance?
Here, we give a rundown of the most interesting loafers that have caught our eyes.