Type of footwear with a sharply pointed toe.

Winkle Picker shoes and boots came to the fore as a fashion item in the late 1950s and early 1960s, and again in the 1980s. They were famously worn by The Beatles when they also became known as Beatle Boots, Beat Boots or sometimes, Chelsea Boots* (Chelsea being the most fashionable area in London, if not the world, at that time).

Winkle picker shoes had excessively long and pointed toes to them, and got their name from the pointed implement used to extract winkles from their shells. The humble winkle, or periwinkle (family: Littorinidae) is a type of sea snail which, when boiled and sprinkled with pepper and vinegar, is quite delicious to eat, - if you can get it out of its shell!

Nostalgia? - I remember that!

As a child, I spent many a Saturday afternoon gathering winkles from the seashore, in preparation for Sunday tea. Once home, the winkles were left to purge overnight in a bucket of salty water to hopefully rid them of all the sand and digested matter (ok, poo!) in their guts. (Unfortunately winkles have a knack of escaping from the bucket and may end up crawling all over the kitchen - the sight of which put me off eating winkles for ever after!)

After boiling for about an hour they were ready to eat. This is where the winkle picker was an essential item. We always used a pin, and things don't come much sharper or pointier than that. It was always quite a challenge to extract a complete winkle from its shell as the thin curly end used to break off very easily. Cries of joy from the various grandchildren indicated success, while the adults in the family seemed quite proficient at it as they quietly munched their way through the plate of seafood.

As an aside, at the same time as I was prising winkles from their shells, I was also begging my mother for a pair of winkle pickers. Thankfully she put her foot down with a firm hand and declined, allowing me to grow up with all my toes in the right place instead of them being deformed into weird and unnatural shapes.

As far as I can ascertain, the term Chelsea boots now refers to boots with an elasticated side gusset. At the time the phrase was coined they had pointed toes as well, but since then the toe shape has changed with the fashion, but the name has remained the same. Thanks to StrawberryFrog for pointing that out. If anyone knows differently please /msg me