- This odd-sounding leather ankle boot became very popular with followers of the Teddy Boy subculture and was later on adopted by the Mods (short for Modernists) in the 1960s. Winklepickers are best known for their long and sharp toes, reminiscent of the long and sharp pins that the British use to take out the soft body parts from the shell of the periwinkle snail. They were very popular with British rock n' roll fans in 1958 and with the punks and the rockabillies afterwards.
- John, Paul, George and Ringo of the Beatles were the first to popularize the Chelsea boots, the modern successor to the riding boots worn by horsemen during the Victorian era. The most distinctive feature of the Chelsea boots are the classic elastic panels on the sides of the boots, called gussets, making it easier for the wearer to slip them on and off when he needs to. In more recent times, the gussets were replaced with zipper closures.
- Chukka boots are also known as turf boots because they descended from the desert military boots worn by soldiers during World War II. They are usually made of suede or cowhide leather with crepe or rubber soles and two or three eyelets. Chukka boots used to be worn by polo players only, but they made their way to the military barracks in North Africa. In the mid-1950s, chukka boots entered the mainstream and became part of casual, everyday style.
- Not every man in 1958 favored the unconventional shoe styles during his time. In fact, the ubiquitous loafer was still in style after Norwegian farmers invented it more than a hundred years ago. Unlike the flamboyant winklepickers and the cumbersome boots, loafers are low-profile and versatile. Plus, a soft leather or rubber sole makes it as durable as working boots. One can don a sleek, black pair to a formal gathering or casual brown penny loafers to work.
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