Usually means: Pointed toe, narrow, elongated shoes.
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We found 4 dictionaries that define the word winkle-picker:

General (4 matching dictionaries)
  1. winkle-picker: Oxford Learner's Dictionaries
  2. winkle-picker: Wiktionary
  3. winkle-picker: Webster's New World College Dictionary, 4th Ed.
  4. winkle-picker: TheFreeDictionary.com

Definitions from Wiktionary (winkle-picker)

noun:  (UK, Ireland) A person who harvests periwinkles (a kind of sea snail) to be eaten.
noun:  An implement used to extract the flesh of a periwinkle from its shell.
noun:  (also attributively) A style of boot or shoe with a severely pointed toe, fashionable in the 1950s and 1960s.

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