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 which gives both the boot and shoe their name is the very sharp and quite 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 pointed toe was called the winkle picker toe because in England periwinkle snails or winkles are or were a popular seaside snack, which is eaten using a pin or other pointed object to carefully extract the soft parts out of the coiled shell, hence the phrase: "to winkle something out", and from that, winklepickers as a humorous name for shoes with a very pointed tip.

Winklepicker shoes, inspired by the Poulaines worn by the medieval French nobility, were a conspicuous contrast to the brothel creepers worn by Teddy Boys. The male shoes were lace-up Oxford style with a low heel and an exaggerated pointed toe. A Chelsea Boot style (elastic-sided with a two-inch, and later as much as two and one half inch, Cuban heel) was notably worn by the Beatles, but although it had a pointed toe, was not considered to be a winklepicker. Winklepicker shoes from Stan's of Battersea were also worn by the Teddy Girls as well as being a fleeting fashion for young women generally.