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.
Deborah Fulsang, "Boot it up," The Globe and Mail, September 15, 2001
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.
—Deborah Sawyer, "Second-hand stores stock one-of-a-kind," The Globe and Mail, May 17, 1980
I also found the following:
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.
Michael F. Bownman, Archive of Scouts-L List, July 2, 1996
By a "pickle-stabber helmet," I assume the author is talking about the classic Pickelhaube (spiked helmet) used by the German Imperial Army starting in the second half of the 19th century. I'm sure there's some kinky connection between the boot and the helmet, but it's too early in the day to think about it right now.