Penny Loafers

Penny for the Chap

in Features by

Liam Jefferies:

As with the Aran Jumper in the previous issue, this article aims to provide a paradigm for the gent looking to source a pair of Penny Loafers suited to his taste, budget, and traditionalist loyalty. Let us begin, as ever, with a look on the attributes of the garment.

Characteristically, the penny loafer is a lace-less, low-worn shoe, akin to the moccasin but for a separate sole and heel. Worn casually, the original intention being a “house-shoe” of sorts one could easily slip on and off.

Penny Loafers

Though Bass undoubtedly innovated the design and added the “penny” to it, the “loafer” model had been around for a few years. This was primarily in the form of the1926 Royally commissioned “Wildsmith” loafer made for King George VI (to wear indoors with his shooting hose), and the “Aurland Moccasin”, first debuted in 1930 by Norwegian shoemaker Nils Gregoriusson Tveranger (influenced by the footwear of the Iroquois peoples of North America) and named after his hometown. This latter model was adopted by the Spaulding Leather Co. to considerable success. The term “loafer” originates from the “loafing area” on a farm where cows are taken for milking; it was here that Norwegian farmers would require a flat, slip-on shoe that could be worn outdoors and avoid dragging mud through the homestead. The first occurrence of the term in its modern use is from an article in Esquire magazine dated 1932.

In 1936 it was Maine-based shoemakers G.H. Bass (originally known for outdoors and aviation footwear) who lowered the throat line and added a distinctive strap to the top of the vamp. The strap had a diamond slit just the right size to hold a penny, ergo the moniker. The shoes were affectionately labelled “Weejuns” to pay homage to their Norwegian roots in design, and to differentiate from the Spaulding model. Later, Bass Weejuns also sported “beef rolls” on the sides of the strap to provide added structural support.

It was writers such as F. Scott Fitzgerald who were first seen wearing such styles on their return to America from their travels overseas. The look was soon adopted by the Ivy League college students and became known as the quintessential “collegiate shoe”, along with white bucks and saddle shoes. Such was the stalwart nature of the Weejun as a college staple that Bass soon had to begin production of a women’s loafer, to match the demand from both sexes. The Weejun had become de rigueur on campus.

Legend has it that, in the late 1930s, Ivy League students would slip two dimes into the slits on their Weejuns, providing the means to make that all-important phone call to Mater and Pater when “school funds” needed replenishing. This soon changed to the shinier penny, as necessity gave way to style. Today, A loafer with a penny inserted provides a coded nod to those other chaps who are “on the level”. American brand Benjos, the people who popularised the Italians’ habit for pairing vibrantly coloured laces with conservative footwear, offers a pair of painted US pennies for $14 – make of that exchange rate what you will.

Like so many items of Ivy League apparel, the Weejun found itself in Britain through the modernist scene of the late 1950s and its penchant for all things American. The penny loafer is one of a few items to survive this entire branch of subculture into its modern incarnations, yet still be favoured by Trad and Suedehead alike. The Weejun has seen itself modelled on countless sartorial influencers, John F. Kennedy, James Dean, Gene Kelly, Michael Jackson (with white socks), and the Duke of Windsor, who first popularised the wearing of the Penny loafer with suits in the 1930s.

How to wear

Penny LoafersIf you are in the market for a seasonal loafer, there are some factors to bear in mind: as loafers are for casual wear, most will be Blake stitched, with the Goodyear welted kind being heavier. Though the layer of cork in the latter does render the shoe more weatherproof, the penny loafer is not something one would don for a yomp in the rain.

While once worn only as part of casual attire, nowadays the loafer can be teamed with a suit and still retain a sense of formality. This is due in no small part to the increase in airport and building security in the 1980s, when time was money and Wall Street stockbrokers could not afford to be held up while tying their laces. As with all leather shoes, regular polishing is required, although there is still an Ivy tradition of subjecting one’s Weejuns to an endurance contest of sorts, letting them become as worn as possible, sometimes even taking to the application of Duct tape to hold them together.

Penny Loafers

Where to buy

Authentic Investor:

Penny LoafersThere is a reason for the term Weejun being synonymous with the penny loafer. For the authentic product, keep strictly to the original design, as this really is the only place to go (£105). Having recently launched in Europe and now available from most reputable merchants, Bass also have some rather contemporary incarnations on their way to our shores, including two-tone suede/high shine leather and a rather fetching example with a thick crepe sole.

Contemporary Modernist: 

Penny LoafersFor the chap with an eye for the contemporary, Yuketen offers its take on the Penny Loafer, in waxed grainy leather with thick soles and a cow-hair vamp (£315). New England based brand Sebago also produce a longer variant of the Penny and, having first beenproduced in 1946, aren’t too far off the mark in terms of heritage (£140).

Gentleman Economist:

Penny LoafersFor the chap on the cheap, as with any footwear, one must avoid the high street at all costs. A leather shoe, be it formal or casual, must be properly stitched and welted to ensure a long life; this tendency makes it all the easier to find a pair second-hand and still in good condition. Make the investment, look after them, and they’ll look after you.

The Chap was founded in 1999 and is the longest-serving British magazine dedicated to the gentlemanly way of life, with its own quirky, satirical take on a style that has recently entered the mainstream.

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