Men's Leather Shoe Designs of the 1950s

Written by crystal vogt
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Men's Leather Shoe Designs of the 1950s
Men's shoe styles of the 1950s included winklepickers, chukka boots and brothel creepers. (George Marks/Retrofile/Getty Images)

In the 1940s, World War II defined what men and women wore since rationing materials was the norm. But fashion changed in the 1950s, when the war was over and people sought out garments and accessories made of quality materials such as wool and leather. With the war as a memory, fashionable styles returned to the forefront of American life. Men's shoes of the 1950s were no exception, and were offered in many different cuts.

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Winklepickers, which were low-heeled, leather ankle boots with long, pointed toes, were popular in the 1950s, according to shoe retailer Underground Shoes, which states that the pointed toe was a counter statement to the more formal footwear of the time. Winklepickers' anti-establishment credentials, according to Underground Shoes, were "enhanced by their appearance on gangs of youths fighting in London Streets or on Bank Holiday beach brawls."

Chukka Boots

Street youth culture during the 1950s often wore chukka boots, according to vintage resource website The Vintage Dancer, which states that chukka boots were inspired from desert military boots worn during World War II in North Africa. Chukka boots are an ankle-high boot made of unlined, suede cowhide. The style features thick rubber soles and two sets of eyelets over the ankle area of the boot.

Brothel Creepers

According to Underground Shoes, brothel creepers gained popularity in the 1950s after British soldiers returned to London from the war. They returned wearing their suede boots, to which they had attached improvised rubber soles made from old rubber tires. Underground Shoes states that these ex-soldiers "crept" their way through the undesirable brothels of King's Cross and Soho in London, giving the shoe its name. Like winklepickers, youth adopted this style because it was anti-establishment.


Shoe retailer Zappo's states that wingtips have been popular throughout most of the 20th century. According to The Vintage Dancer, wingtips were worn by conservative men in the 1950s because the style was seen as classic and elegant. Wingtips get their name from the stitching design that looks like the letter W on the toe of the shoe, according to Zappos.

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