The slip-on forefather of the penny loafer was a style first worn by Norwegian fishermen and adopted by Ivy Leaguers in the 1900s travelling to Scandinavia. Trademarked as “the Weejun” (derived from Norwegian) by US shoemaker GH Bass in 1936, this version with the now familiar band (or “saddle”) across the upper – inside which students are said to have stashed pennies for a phone call – became an iconic design thanks, in part, to being seen on preppy poster boy JFK. The penny loafer also found favour with everyone from fans of rockabilly to beat poets and mods. David Hockney and Steve McQueen were fans. Michael Jackson even wore a pair in his 1983 video for Thriller. Its distinct yet understated style is the definition of versatility – and ripe for a revival.
Take GH Bass’s current collaboration with cult US brand Engineered Garments, which features asymmetric crocodile and other reptile-effect patterns (£195). Teamed with blue denim or chinos, they give a casual look some kick. Textural Ivy League luxe can also be found at Santoni, where penny loafers come in deep navy blue (€570) or rich chestnut brown woven calfskin. There are also Jimmy Choo’s Darblay loafers in buff (£450) or navy suede with a plush Kevlar-like woven top panel. The brand’s new graphite-grey Darblay style (£525) is a highlight, too, with its removable Choo coin etched with the stylised silhouette of a woman. Christian Louboutin has also designed its own coin, which sits in a cross strap that evokes a heraldic scroll unfurled across suede or patent-leather loafers (£815).
I’ve long paid attention to this “slot” shape on loafers and have enjoyed how the motif evolves every season at Prada, where I’ve been sourcing penny loafers for clients for over a decade. I’ve seen everything from elongated, futuristic V-shape slots to ones made of metal – while leathers change from classic or full-grained calfskin to high-shine spazzalato. Soles are sometimes rubber, and this season there’s a black leather penny loafer (£460) with a trainer sole.
Harrys of London has also created a sporty version: the Edward loafer in soft, unlined deerskin (£450) and calfskin suede (£395) with super-light leather soles and patented 3D Technogel inner soles for added comfort, improved weight distribution and shock absorbency. Its modern, swept-back profile is cool and low-key and is especially natty in green – which would look great teamed with similar colour trousers.
There are more lightweight loafers at John Lobb – the Lopez (£940) with its new-style chunky, rubberised EVA “lighter than air” Goodyear welted sole. Hermès’ marine calfskin Ronald loafer (£770) with an “H” emblem in place of a slot also has a voguish lightweight moulded sole.
For colour, look to Paul Smith’s Glynn penny loafer, which comes in a variety of colourful suede (£275) and leather (£285) models, from ochre to hot pink, though turquoise and olive green are my favourites. Santoni has some cracking-coloured suede pennies too. The Carlos (€460) in cement or mink is best with summer tailoring. Coloured loafers can really liven up suiting – I team my slouchy Anderson & Sheppard fawn Fox flannel suit with a burgundy pair.
Manolo Blahnik sports A&S suits too, often in striking colours. His exuberant style can be found in mauve penny loafers (£695) with additional fringing and punched wing-tip brogueing, rather like Dandy golf shoes (less bold are versions in ochre, brown or black). More statement-making pairs can be found at Church’s, where the Pembrey Met loafer (£380) in black or burnished tan has been updated with studs. These would make great cocktail shoes for those keen on breaking with tradition, as would Louboutin’s ornate Dedonaki (£875) with baroque cross straps with gold and red flourishes.
Less dramatic, but equally original, are Thom Browne’s muscular penny loafers (£760) in pebble-grain leather with a black thick crepe sole. Other styles feature the brand’s signature red, white and blue webbing strap and lightweight rubber sole (£760) and red, white and blue stripes running through the sole (£1,020). I’m not sure if they’d be JFK’s style, but their contemporary cool captures the sure-footed strides forward penny loafers are taking this season.