By 1936, Hutton had created a completely new style of shoe with its patented plantation cradle sole construction, the ‘Play-Boy’ as it was originally called. The new construction method involved attaching the natural Crepe rubber sole to the shoe by sewing it directly to the body, or ‘upper.’ As an accent, a piping detail was then sewn horizontally all around halfway up the sides of the shoe. The exposed join and lower part of the piping were then covered by an inch-high (2.5cm) strip of Crepe ribbon, or ‘foxing’ all around the sides of the shoe to complete the unit. The new shoe was marketed as “The Easiest Shoe In The World,” and for the first ten or so years of its production, the Playboy was aimed at the Sport and Leisure markets, described as being the ideal shoe for Golfing and walking, or, “Designed to cover both ‘Spectator’ and ‘Active sports occasions,” along with town wear.

During the WW2, along with other brands, Play-Boy shoes and the ankle high Chukka boots were heavily exported, mainly to America and Australia, as a large part of Northampton’s shoe industry was mobilised to export goods in order to earn valuable foreign currency for the nation. In December 1947, an interesting snippet by, ‘Esquire’ a journalist for the New South Wales Daily Telegraph noted, “Those heavy-crepe-soled “desert brogues” that we used to buy for a song in Cairo (and call by another name) are now selling in the city at about £6 a pair.

Earlier that month Esquire also wrote in the Sydney Morning Herald for the Farmer’s department store column: “NOW, HOW ABOUT another £6/6/- for your sports shoes -… The Ground Floor Shoe Man, who practically walks with a stagger under the weight of his big brain, has introduced to Sydney what is probably the last refinement in foot-toggery. Playboys by Hutton of Northampton. The shoe and the chukka boot- in suede. Esquire slipped one on and it was like being foot-massaged by Miss Australia. His feet have been going around saying cutting things to his shoes ever since. The chukka boot, as worn by Eighth Army officers on the verandah of Shepherd’s Hotel under corduroys and guardsman moustaches. In soft, brown suede with heavily tractioned crepe-rubber soles which will wear as long as your feet. The chukka boot. £6/5/9. The Playboy shoe. £5/9/3, and well worth five minutes of any Esquire’s time merely to drop by to see.

So, were Playboy shoes and boots worn by serving officers in Egypt during WW2? -it seems quite possible, according to Merton Nadler in his book “Young Man, You’ll Never Die,” he states:

“We bought fly-whisks and crepe-soled chukka boots, known as brothel-creepers, and slinky khaki slacks of exquisite sea-island cotton. It was only later that I learnt how they came to be available from the street vendors, and how large quantities of military stores and supplies of every description, from food to clothing, from armaments to engine parts, from liquor to vehicles, were ‘liberated’ by unscrupulous storekeepers, British officers as well as NCOs and men, and sold for personal gain to local dealers.”   Merton Naydler. ‘Young Man, You’ll Never Die’

What is certain is that the Playboy shoe brand was well established through national and international magazine and newspaper advertising since its first year of trading, the extra comfortable walking and leisure footwear had been widely adopted by sportspeople, golfers and the well-to-do. For the first few years of the war, it is widely known that officers in certain military units were shown some leniency when it came to uniforms, with private purchase items often used in preference to the more cheaply made issued goods. So, it is quite possible that officers of the Eighth Army took their own Playboy shoes and boots to Egypt with them or bought ‘diverted’ items in the souks of Cairo, as shown above, it was also at this time that these crepe soled shoes were nicknamed ‘Brothel Creepers.’

The 1950’s saw the Playboy adopted by early British Teddy Boys and Ivy League types, Steve McQueen adopted the Playboy Chukka boot as his favoured item of footwear, wearing them as early as 1956 in the stage production of A Hatful of Rain as well as on film from 1958’s The Blob right through to Bullitt and The Thomas Crown Affair both in 1968, Playboy’s original Chukka boots were also his preferred daily wear during this period. Jazz legend Miles Davis wore Playboys for his 1958 Milestones album cover photo session.

The 1970’s saw a rebranding as the shoes and chukka boots were rebranded as The Original Playboy, the heels and soles also became thicker and chunkier for a newer look. Again, advertising in the USA, Canada and Australia showed that exports continued to be strong. Previously, plain suedes and leathers had been Playboy’s mainstay, but now two-tone black and white brogues, elasticated sided, twin-buckled and multi-coloured combinations entered the range. The November 1971 issue of Ebony magazine, USA, carried ads by the Original Playboys new distributor, John Winter & Son of New Jersey, showing the above styles, the Playboy shoe was increasingly crossing over into street-style.

Meanwhile, over in the UK, Malcolm McLaren & Vivienne Westwoods’ Let It Rock shop on the King’s Road also stocked a rare custom-ordered pointed toe version of the Playboy shoe. Mid-decade, the pre-Stray Cats, back-to-the-roots British Rockabilly scene of the mid-70’s saw Playboy chukka shoes and boots worn with jeans and Donkey jackets, a reaction to the Rock ‘n’ Roll world of the longer-haired Teddy Boys with their increasingly brightly coloured drape jackets and creepers, which the rockabillies viewed with disdain. Clash manager Bernard Rhodes was also a wearer.

As the 1980s rolled around, Original Playboy shoes were very much a part of the exploding Hip Hop scene, known wearers being the Rocksteady Crew’s Popmaster Fabel and Ron La Retro, who, in 2019 went on to organise an exhibition titled ‘Forgotten Street Fashion’ at the Universal Hip Hop Museum in the Bronx, New York. Other famous wearers being Brooklyn’s own Beastie Boys.

During 1990’s and 2000’s a series of books by black authors documenting their youth in the 1960’s and 70’s saw release in the United States, among them.

Blood Posse. Phillip Baker. 1994 (1970s Brooklyn life)

On The Job, A Warrior in Blue by Lux Jameson. 2000 (1960s life onward)

Living to Tell, Collected Memoires by Eddy Douglas Brown. 2001 (1970s life)

Away from Mothers Watchful Eye by Jesse A, Mayfield. 2009 (1960s life)

The Rat That Got Away, A Bronx Memoir by Allen Jones. 2009 (1960s life)

The Pop-Up Kid, Secret Memoires of the Internationally Abused by Noah Jacobson. 2014 (1970s life)

The Kings of Dance, The History of Bronx Rock by Luis De Jesus. Jan 2015 (1970s life in the Bronx)

47 years later Charlotte still works with the Original Playboy and in recent years has taken it to new areas, 2021 saw the beginning of a collaboration with the Steve McQueen estate, something which seems only natural due to McQueen’s long association with Playboy shoes, as seen in film, on the stage and as documented in photographs of his private live during the 1950’s and 1960’s.