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1.
Apparently an old phrase used to describe shoes with very narrow toe at end.
I was wearing my new winkle pickers.
by Rob1976 January 14, 2006
 
2.
big long pointy shoes, worn by leprichauns and irish folk alike.
"will you fuck my shoe" a common phrase in germany.
by Carlos August 11, 2004
 
3.
on morcambe bay, there are a bunch of dead koreans that drowned a while back after gettin stuck pickin winkles illeagally. they looked tired, slanty eyed, and mauled.
after a heavy night on the piss dan saw dave who was looking dog rough. dan sid unto dave " fuck me, you look like a damned winkle picker!
by Big Dog July 07, 2004