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The Shoe Styles I've Known of: Penny Loafers

Updated: Apr 10, 2022

(Photo from Voxsartoria)

Like another notable option in this versatile shoe wardrobe – the split toe derby – this model ostensibly has its origins in Norway. Although gentle research shows most footwear ‘origin stories’ to be either apocryphal or downright marketing fantasies.

According to most sources, the humble penny loafer began life as a simple slip-on shoe made for Norwegian country homesteads and resembling modern-day Ugg boots more than what we recognize as penny loafers. These minimal shoes were easy to slip on to milk the cows or for a spot of weeding.

The industrious G.H. Bass noticed this style while traveling through the country and thought that such practicality would also be perfect for students late to class, or for running out quickly to the supermarket. Thus, he changed design elements to provide a sleeker upper of lined leather and attached soles more suited for city sidewalks than small plots.

Interestingly, despite the obvious similarity to traditional Native American moccasin-style shoes, this was never acknowledged in the final design or marketing. Apparently ‘Weejuns’ was considered to be a more appealing name for the ‘WASP’ target market than ‘Wiyots’. Ironically, the Norwegian tese shoes that had originally inspired Bass had been taken directly from a classic Iroquois design in the 1800s. Despite the muddled origins of this style, the shoe met with instant popularity upon release in 1936 with the aforementioned students and suburbanites.

Iroquois mocassins. (Photo from the Metropolitan Museum of Art)

During the mid-century years, the etymology of the loafer took another turn. Cash-strapped students are said to have started using the loafer as utilitarian devices by placing a penny into the decorative vamp strap. Thus any requirement for a long-distance phone call or bus ride could be met with no ‘out of pocket’ expenses… This ‘penny loafer’ style came to be immortalized as the Ivy-league standard, appearing in period classics like The Graduate, Ocean’s Eleven and Plein Soleil, and worn by Cary Grant (with a dinner suit no less!) and JFK aboard his sailing boat in Hyannis Port.

Browse the iconic Take Ivy photograph series for perfect examples of penny loafers worn with a certain nonchalance that only entitled university students can seem to muster. Worn with off-white socks, chinos, oxford cloth button-down shirt, and Shetland sweater, this look has become so indicative of a time and place as to be considered a trope. What many seem to miss, however, is that this style so effortlessly harmonises with a whole range of sportswear, refined casualwear, relaxed business-wear, and casual suits.

Pennies in their ancestral home. (Photo from Take Ivy)

The style is perhaps at its’ most versatile in shades of brown calf and suede, although proponents suggest black calf and country grains, cordovan, and even exotics in some cases. Along those same lines of versatility, the author would contest that a round-toed last, higher vamp and top line, and restrained apron detailing will provide the opportunity for most wear.

The strap can be partial or full and may include a ‘beef roll stitch’ on more rustic styles. The apron may be hand or machine sewn, although this detail tells little of the overall quality of the shoe, and paradoxically the handwork may actually detract from the overall formality in a manner similar to handsewn gloves.

Outsoles can be found in rubber, although single leather is traditional for this shoe, and perfectly matches the casual and comfortable three-season design. Although differences do exist at all levels of expenditure, these are usually of a materials and construction nature, as opposed to large aesthetic variations.



The attainable range has some stunning options, as befits a popular style like the penny loafer. Due to its ubiquity and the age of its design, many heritage manufacturers have well-evolved styles that have endured for decades. Newcomers to the segment also provide some very tempting options and should be considered alongside the more established brands.

At this level, you should expect high quality, but perhaps not flawless uppers in calfskin. Suedes and grain leathers are a fantastic option in this price category and provide an excellent price-quality ratio. Either fully leather-lined or unlined are both options, along with a full leather insole. The best of breed uses a Goodyear welted construction, although there remain strong arguments for using Blake rapid construction for this design due to its’ increased flexibility and low profile.

Option 1: Allen Edmonds Randolph in Dark Chili

(Photo from Allen Edmonds)

The Allen Edmonds Randolph presents a very strong case for inclusion, being built in the USA with very classic design elements. A hand-sewn apron reinforces the Ivy credentials of this model as does the very fetching ‘Dark Chili’ colour, which could be taken in many different directions with the use of pigmented conditioning crème polish.

Adding to the details are a full strap and a very balanced shape from the form provided by the round-toed 79 last. The single leather sole is 360-degree Goodyear-welted to the upper, and has an extremely comfortable cork-filled midsole and full leather insole. Adding to the versatility is the fact that this model is available in no less than ten width fittings, which can be very important for loafer fit, as heel retention is key.

With its traditional design details, this model would scream Ivy-league if paired with off-white socks, mid-wash blue jeans, white OCBD, and a herringbone Irish tweed jacket.

Option 2: Löf & Tung Xavier in Polo Suede

(Photo from Skoaktiebolaget)

The slightly dégagé impression of this loafer actually belies a very Anglo-American inspired loafer by Swedish/Spanish Löf & Tung. Uppers in a tonally warm ‘polo’ Repello suede by English CF Stead, and patterning with a high vamp and top-line help to distinguish them from more Italian-inspired loafer offerings.

The single leather sole is wonderfully finished with a closed-channel stitch and beveled waist edges. The lovely round toe high-walled R last is used for this model. Its dimensions perfectly suit both mid-century styled loafers and classic Budapester-style full brogue derbies. This model is fully lined in veg-tanned leather and has a full leather insole and cork midsole for conformability.

This pair would sing worn sans chausettes with a pair of off-white cotton trousers, light denim unstructured collar shirt, and a navy Shetland worn loosely around the shoulders for an Italian-inspired summer look.

Option 3: Loake 1880 Whitehall in Black Calf

(Photo from Herring Shoes)

Although most commonly associated with shades of brown, black penny loafers can be worn to great effect in certain situations. This pair - by English stalwarts Loake - provide the opportunity to step up into another level of formality (the name Whitehall is the colloquial term for the British governmental apparatus).

Lasted in England (the uppers may be sewn in India) on the 025 last, this model has a sleek ‘modern round’ toe and slim foreparts that may not suit the wider foot. Restrained ‘seagull’ strap and a nicely finished open-channel sole stitch complete the harmonious design. The uppers leather is a good - if not excellent - quality calf leather with a moderately fine break.

This style of loafer could be enhanced by a mirror shine on the toe and heel counter. Using a navy or red wax polish for this process will add depth and dimension to the leather that black polish alone cannot match.