L: What a Winkle Picker actually is
R: Along the lines of what I imagine a Winkle Picker would be
However, Winkle Pickers actually have nothing to do with male genitalia, aside from their history. You see, Winkle Pickers were inspired by the Poulaines (the long and exaggerated pointed toe) on shoes worn by male nobility in the Middle Ages. Much like pants, what began as a style worn exclusively by males, did not remain that way: on came the 1950s and women too could join in the winkle picking fun.
The original Winkle Pickers (and what could also be an illustration of winkle picking). Evidently, leggings worn inappropriately as pants also dates back to the Middle Ages.
In the middle of the 20th century, winkle pickers became popular in Britain among fans of that crazy music we call Rock & Roll. As the years progressed, the popularity of these shoes with pointed-toes grew like a pubescent teenager and have been worn by a variety of subcultures around the globe. Currently, winkle pickers are very popular among German goths (but typical of goth non-comformity, they call them "Pikes" ) and The Kings of Leon.
Let's get back to the issue at hand, the uncomfortable term: winkle pickers. Unlike The Pussybow, a reason exists for the terrible name given to these shoes. According to the most reliable source on the internet, Wikipedia,
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, winkle-pickers as a humorous name for shoes with a very pointed tip.There you have it folks. Winkle pickers, in fact, have nothing to do with picking winkles, but are simply a style a footwear named by some freaks eating escargot via pin on the beach. This explanation has done absolutely nothing for my unease with the term and winkle pickers will forever remain a term in fashion that makes me uncomfortable.