Winklepickers, or winkle pickers, are a style of shoe or boot worn from the 1950s onward, especially popular with British rock and roll fans such as teddy boys. 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 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 or myggjagare, literally "Mosquito chasers". They are still popular in the goth, raggare and rockabilly subcultures. In some parts of the U.S. they are called "roach stompers".