Green’s Dictionary of Slang

highly pointed-toed boots or shoes; occas. in sing.

1963		N. Dunn Up the Junction 1: Hey, look out, yer steppin’ on me winkle! [Ibid.] 11: Her green winkle-pickers stand neatly against the wall.
1969		N. Cohn Awopbop. (1970) 18: Teds wore drainpipe jeans, three-quarter length jackets, winkle pickers.
1978		Observer Mag. 14 May [advert for Clarks shoes] 2: Even a short trip down memory lane reveals the winklepicker (y-e-o-w!).
1987		(con. 1920s) L. Redmond Emerald Square 102: Gleeson wore oxford bags, trousers with twenty-four inch wide legs, pointed shoes, winkle pickers and jazzy waist-coats.
2000		Indep. on Sun. Rev. 30 Jan. 7: A 56-year-old shaven-headed libertine in skintight trousers and winklepickers.