Wikipedia
Winklepickers, or winkle pickers, are a style of shoe or boot worn from the 1950s onward by male and female British rock and roll fans. The feature that gives both the boot and shoe their name is the very sharp and long pointed toe, reminiscent of medieval footwear and approximately the same as the long pointed toes on some women's high-fashion shoes and boots in the late 2000s.
The extremely pointed toe was called the winkle picker because in England periwinkle snails, or winkles, are a popular seaside snack which is eaten using a pin or other pointed object to extract the soft parts out of the coiled shell carefully, hence the phrase: "to winkle something out", and based on that, winklepickers became a humorous name for shoes with a very pointed tip. Other countries had other humorous names, e.g. in Norway and Sweden they were called myggjagere/myggjagare, literally "Mosquito Chasers". They are still popular in the raggare and rockabilly subcultures. In some parts of the U.S. they are called "roach stompers."
Usage examples of "winklepicker".
Omally chose for this special occasion a Hawaiian shirt that his best friend Pooley had given him for Christmas, a dove-grey zoot suit he had borrowed from this selfsame Pooley, and the aforementioned winklepicker boots, which in fact were also the property of the also aforementioned Pooley.
On his right foot a black patent leather shoe, with a winklepicker toe and a high stiletto heel.
The siblings, pickled in hatred, shuffle out onto the English-style lawn, where they deliberately trample several costly blossoms and grasses and leaves underfoot, beneath soles paper-thin, because the shape of fashionable winklepickers would be spoilt by re-soling.