Updated: Apr 10, 2022
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.
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.
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
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
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
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.
This pair could be worn for business occasions with the correct accoutrements. Under a navy twill suit, with burgundy socks, a white shirt, and black and white prince of wales tie these shoes would provide a subtle ‘high/low’ combination that would still pass muster in most offices today.
As stated before, the progression upwards through price tiers does not provide a massive change to the overall aesthetic of the shoes in the same way as would an oxford or derby. Rather, the internal structure of the shoes and quality of the leathers used will incrementally improve. Unlike many areas in today’s world, the quality of men’s footwear does bear a strong relationship to the price paid, at least within the welted shoe sphere.
At this level, expect very fine calf leather uppers, suedes, and even cordovans in classic colours. Lasts may be slightly more refined or may equally be more rustic depending on the intent of the maker. Choose well, as these may be your casual companions for life…
Option 1: Carmina 80708 Unlined full strap loafers in Brown Vegano
This model - by Mallorca-based Carmina – brings a European sensibility to this design. The UETAM last has a distinctly Italian-inspired shape with a slightly pointed toe and low instep. It will suit those with a low-volume foot very well.
The unlined nature of this shoe, as well as the slightly lighter mid-brown colour will perfectly suit summer wear, although one should be mindful that the uppers are chromium-tanned and may not work against everyone’s skin. Carmina should be commended for specifying the upper leather, which paradoxically becomes rarer as one moves up the price gradient.
In this case, Annonay’s Vegano is used, a high-quality French calfskin that is only partially finished in the tannery. This allows the manufacturer to finish the skins to their exact desired colour. It also allows for extra antiquing and burnishing which accelerates the development of a unique patina over time. This shoe also sports a full strap and high-quality closed-channel sole stitch.
Given the sleeker last of this model, a more formal outfit to pair with would be ideal. Perhaps a lighter grey summer wool suit, blue shirt, and navy ancient madder silk tie would work nicely.
Option 2: Crockett & Jones Boston in Dark Brown Suede
Crockett & Jones’ entrant shares several visual similarities with the aforementioned Löf & Tung pair, from the Repello suede uppers, high vamp and top-line and high-walled round toe last (the 314 last in this case). This might lead you to assume that the Xavier’s are a screaming deal, and that these Boston’s are overpriced… Well, yes and no.
The Löf & Tung pair is indeed a very good deal, but the difference is perhaps more than would first appear. Firstly, the upper leathers are expertly scrutinized by C&J’s exacting clickers and the heel stiffener is leather rather than leather-board. Further, the lining leather is in another league as far as comfort goes, and the ‘Made in England’ stamp carries a price tag of its’ own. The Xavier does indeed have finer finishing details like beveled waist-edge, closed-channel stitching, and even arguably better sole materials, but the Boston is undoubtedly a finer shoe.
In brown suede, the sheer versatility of this model could work with a casually worn suit, all the way down to jeans and a sweatshirt. The author’s preference is to wear them with olive chinos, navy socks, a blue and white university stripe oxford shirt, and a navy Barbour waxed cotton coat.
Option 3: Alden Full strap loafer in Colour 8 Cordovan
Alden has a strong track record of producing models in this design and is considered by many to be the ultimate maker for penny (and tassel) loafers due to its’ long and storied connection to the Ivy League (Alden’s full name is Alden of New England).
This model is one such classic design, in another classic material — colour 8 cordovan. Interestingly, the colour 8 cordovan from Alden appears a slightly darker shade to other makers, as they add another coat of pigment at the factory. What this does is provide a richer colour that can uniquely bridge formal and casual outfits, aided by the gentle sheen and lovely ripples formed on the membrane’s surface over time.
One could equally recommend the classic Leisure Hand Sewn (LHS) loafer here, which lacks the full strap detail, but is available unlined for summer, and is arguably the more classic design. This loafer is built upon the Aberdeen last which - while being Alden’s narrowest – still fits true to size with a ‘modern round’ toe.
Once again, this model’s heavy Ivy league connotations would work wonderfully alongside similarly thematic items. A heavy pink oxford shirt, worn under an LL Bean Norwegian fisherman’s sweater and paired with heavy brown corduroy trousers would certainly provide a strong visual link.
Highest-grade materials, scrupulous quality control, and bankable brand recognition are the hallmarks of loafers in the aspirational price bracket. They typically remain Goodyear-welted, with calfskin uppers and single leather soles, although examples can be found that disrupt this formula. No compromises should be made when paying this price for shoes, and retailers will typically ensure perfection either in-store or via online commerce sites.
Look for unique and antiqued leathers, perhaps exotics* or cordovan in rare colours like ravello, whisky, or mahogany. Upgraded materials like oak-bark tanned outsoles and insoles, kid leather linings, and full leather heel and toe stiffeners can also be expected here. Within the relatively defined design format of penny loafers, some more unique design elements may also be encountered in this range.
A quick word on exotics, as it is in this style that one will most likely encounter uppers of crocodile or alligator. If buying shoes containing the skins of rare or protected animals, ensure that they are certified by CITES (the Convention on the International Trade of Endangered Species of wild flora and fauna). It is the consumer’s responsibility not to support the illegal trade in skins, which does untold damage to many species and ecosystems around the world.
Option 1: Edward Green Piccadilly in Dark Oak
Despite the extremely classic styling of these penny loafers, they remain very popular with well-dressed men around the world due to their well-balanced design and peerless quality-control. Edward Green shoes can be found in most major global centers of commerce, and as such, represent to many the zenith of English factory-made footwear (although Gaziano & Girling may be challenging that reputation currently).
This model — the Picadilly — is built on the round-toe 184 last, which was specially designed with a tighter heel clip, lower instep, and narrower waist for a perfect loafer fit. In Dark Oak - one of Green’s most beloved shades – they work well in almost any situation, although the darker burnishing of the heel and toe and subtle colour variegations might best work with more tailored elements. Perhaps a casual suit in tobacco Irish linen, with forest green socks, light blue shirt and green, blue and brown Macclesfield tie for a summer daytime event.
Option 2: JM Weston 180 Loafer in Black Boxcalf
JM Weston has provided the shoe world with another robust classic in form of the 180 loafer. This loafer features the very high-walled 180 last which is quite roomy in heel and instep and features patterning with a high top-line. Thus, this model may not fit all feet equally well and one would be wise to try these on prior to purchase.
This model also features a unique split-toe design under the apron - which has a distinctly high ridge - and a ‘seagull’ strap. Weston is known for their use of high-quality Bastin & Fils outsoles which are slow oak-bark tanned to provide fantastic longevity. The upper leather is unspecified, although given that Weston owned the French Tanneries Du Puy for several years, that may be a solid bet. In any case, it is a very high-quality and finely breaking calfskin that will reward care with a lovely glow.
The juxtaposition of very casual design and very formal leather on this model present something of a conundrum for the styling segment. Given their French heritage, perhaps an injection of French monochromatic chic is suitable. Charcoal twill trousers and socks, a marled grey cashmere polo neck sweater, and black and white herringbone wool sports coat would provide a very tonal backdrop for these shoes.
Option 3: Enzo Bonafe 3978 in Mahogany Cordovan
Another beautiful full-strap design, here in a rare shell cordovan from Italian hand-makers Enzo Bonafe. But far from ‘all style and no substance’, this model truly delivers with near-bespoke levels of make including hand-lasting and hand-welting, hand-stitched aprons, and hand-finished uppers.
Touching so many skilled hands in the process of creation imbues these shoes with more character and life than any factory-made shoe could possess. Here, this character is amplified by the 74945 last, which pairs a very low toe spring with a dramatic sweep up at the instep. These shoes truly possess the visual presence of bespoke pairs costing many factors more, and if the last works for your foot, one will experience scant improvement moving to the latter.
The mid-brown mahogany colour and subtle sheen of this shoe would suit mid-grey flannel trousers perfectly. Paired with a traditional double-breasted navy blazer with antiqued brass buttons, and an ecru submariner’s sweater, this would provide a look befitting Sir Roger himself…
When a dress shoe is paired back to its’ fundamentals; an enclosed toe and vamp, leather sole, and cupped heel, one starts to approach the design parameters of the penny loafer. As has been the case since the days of Beau Brummel, elegance in male presentation has been a slow movement towards essentialism, comfort, and proportion.
In denying the laces of an oxford, the extraneous patterning of the split-toe, the external facings of the derby and the decorative punchings of the brogue, the penny loafer became a style icon not unlike the Beau himself. By disregarding the unnecessary, one might find a true and honest style that fits one’s life, a lesson to be learnt by all. And as for those of us bitten by the style bug, we have one last guiding word from the late Diana Vreeland, who maintained that ‘elegance is innate, it has nothing to do with being well-dressed. Elegance is refusal’.
The next installment in this series will introduce the equestrian boot par excellence; the Chelsea.
Disclaimer: Any views represented in this article belong solely to the author and may not represent those of the blog owner. This article is not sponsored by any brands.
Photography: as stated