n. A boot with a high, thin heel.
2001
The high-heeled, pointy-toed boot was the trendsetting footwear on the designer runways this season, but that doesn't mean those skittish about pickle-stabbers need worry.
1980 (earliest)
Footwear in good condition presents the biggest supply problem for the Lockharts, although they have managed to acquire several pairs of pumps with pointed toes and stiletto heels — variously called winkle-pickers or pickle-stabbers — and Courreges disco boots (white with clear plastic inserts at the top), which sell out very quickly because they go well with today's styles.
On the other hand, if a Troop decided to adopt a hat not in harmony with Scouting, I'd expect a quick reaction; e.g., a Troop that adopted a pickle-stabber helmut [sic] with skull and cross-bones logo, probably should expect to be told in short order to stop the practice.