It was originally known as the Weejun, a mispronunciation of the more understandable Norwegian, because, well, it was imported from Norway. Legend has it that Norwegian fishermen used this type of footwear, in which the upper part and the sole were made of a single piece of leather, when they were strolling through town, unable to take to the high seas. It was the American firm G.H. Bass who registered the patent for the brand and launched the reputation of this shoe, which evolved into the Loafer: although with a separate sole sewn onto the upper part, the very name itself conjures up in the mind someone who has either no desire or no time to lace up his shoes in the morning.
The penny loafer is merely a pimped up version of the classic loafer, with a smooth vamp. The lip-shape on the upper part was apparently inspired by Alice Bass, the wife of the aforementioned industrialist G.H. Bass: she was in the habit of kissing her shoes, and so unwittingly gave her husband the idea to create moccasins with that form on the toe cap.
The popularity of moccasins is mainly down to Fred Astaire, who used them in his tap-dancing routines on film, and was also partial to partnering them with an evening suit… University students of the 1950s got into the habit of slipping a penny – the same ones used in phone booths - into the slit-mouth on the upper part of the shoe, thereby setting off a craze that spread like wildfire across the globe.
To those in the know, the Piccadilly by Edward Green is unanimously considered to be the penny loafer par excellence: classic, with a rounded tip, a Goodyear sole and fine finishing touches. It has rather a high instep, leaving little uncovered, and is mainly suitable to accompany formalwear, paired up with an evening suit as the black colour suggests, although the brown tones and the suede versions could easily complement denim or jacket and trousers. Besides, the sleek and harmonious lines of this loafer profile are not something so easy to find on the market: many low quality footwea have their tip pointing upward, a style choice I would prefer to ignore.
I opted for the size 8.5 F, seeing as the E was too tight on my instep, and I followed the carefully given instructions of wearing the shoes in gradually, avoiding all-day wear on the first occasion. The result? They took shape after two or three wears, and now they are as comfortable as slippers. The Piccadilly is available in various colours and leathers at this link.
Just one last piece of advice: so as to avoid blatantly offending (indeed, torturing!) aesthetic sensibilities, please remember that that when wearing black shoes, blue socks are to be shunned.
Bespoke hugs,
Fabio
