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.’