If you were to ask the average person on the street what a winklepicker was, there's no telling what the person might say.
On the other hand, there is something slightly suggestive about those four syllables that might lead one to think it might be slang for something sexy. All of which leads to the next question, just what sort of "winkle" requires a "picker"?
A "winkle" is an English-term meaning a water snail (usually cooked in the shell and sold in pints along with some vinegar by a street vendors). "Winkles" are eaten with a pin or pointed object to get the winkle out of the shell (hence the term "to winkle something out").
However winklepicker usually refers to a style of shoe or boot worn in the 1950s onward by both male and female British rock and roll fans. Reminiscent of medieval footwear worn by jesters and today by pop stars, the feature which gives both the boot and shoe their name is the very sharp and quite long pointed toe.