"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
I thought this term was much older, but the earliest citation I could find dates only to late last year:
"To balance his drag-king masculinity, he added patent-leather pickle-stabber high heels and emphasized womanly curves with Madonna-esque satin bras."
—Canadian Press Newswire, December 21, 2000
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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
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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.
