As long as I have had an interest in classic menswear I have had a keen eye for loafers.
I don't know why, though one logical explanation might be that when I started my career in the honest service of style 16 years ago I worked for Ralph Lauren. This brand with their deep roots and heritage in the American preppy and IVY style has always, rightly so, had penny and tassel loafers as an integral part of their style and offering. I bought my first penny loafers and tassel loafers (of course made my Crockett & Jones for Ralph Lauren) at this time and have favoured them ever since!
Loafer is a term from the US that most likely originated in the 1930s and is the general term for slip-on shoes. There are many versions today such as the horse-bit, car shoe, moccasins, slippers, Belgian shoes, lazy-man etc. but I shall focus on the two most important, the penny and the tassel loafer.
It’s hard to say exactly where and when the penny loafer was created. Some say that they most likely have their origins in London in the mid 1850s and were created as a casual house shoe for the King George VI. Other sources state that they are from Norway and called Norwegian shoes though of course it’s hard to tell.
They became very popular during the 1940s leading through the 1960s in the US and subsequently a crucial part of preppy and IVY culture. The little diamond shaped piece on the uppers is said to have been used by IVY students to hide a coin…
The tassel loafer was created subsequently and has seen a huge revival during the last 5-6 years. One reason may be that the model, being very popular in Italy for decades especially in brown suede, worn by stylish gents without socks and with soft constructed suits was taken up by the masses. Since the Italian style has had a huge influence on the revival of menswear in last 10 years the suede tassel loafer takes centre stage in that.
I see the Cavendish loafer in Polo Brown Calf Suede all the time here in Sweden. I would say that it’s likely the most popular summer shoe among the well-dressed Swedish Gentlemen during the warmer season.
Personally my favourite model this season is the Harvard penny loafer in Shell Cordovan. I will wear it with a cotton suit, pinpoint oxford shirt, knit tie and a linen pocket square for the next coming four months.
I was recently asked which model I prefer if I had to choose between the penny and the tassel loafer? Well let me answer that question the rational way through an inventory of my dressing room. I own the following loafers from Crockett & Jones: Harvard in Dark Brown Cordovan, Boston in Dark Brown Country Calf Grain, Henley in Burgundy Shell Cordovan and an old pair of Lincoln in Chestnut Calf all pennies. In opposition stands my Cavendish in Polo Brown Calf Suede lonely, though defiant. Alas, 4-1 is a pretty confident victory for the pennies against the tassels, clearly demonstrating I am a penny loafer kind of guy…