Sly Boots

Cousin of Sneaky Pete.

Dear Word Detective: Would you be able to tell me about the origin of “sly boots”? It is a funny way to describe someone who is acting like a “sly dog,” but I have no idea where the saying came from (or even where I personally picked it up!). Thank you for your assistance. — Miriah P., Illinois.

Oh no, thank you. You just saved me from answering a question about football terminology. I had been staring at that question for a half-hour, at a complete loss for words, when your email arrived. I think it’s fair to say that I regard football with the same degree of enthusiasm the average person has for being trapped on a elevator with Alan Greenspan. Yet I have learned from experience that football fans are sensitive folk (putting it mildly), and do not respond well to gently mocking levity, my usual resort in such cases. Trapped twixt the Scylla of catatonia and the Charybdis of having to change my phone number, I’ll gladly jump ship to “sly boots.”

You’re not the only one who is having trouble remembering where you first encountered “sly boots.” My guess is that we both first ran across it in some bit of classic English literature, one of those Penguin paperbacks we bought, at least in part, because we liked the painting on the cover. I also, for some reason, associate the phrase with Beatrix Potter, but that may just be some crossed synapses in my noggin.

In any case, the Oxford English Dictionary defines “sly boots” as “a sly, cunning, or crafty person; one who does things on the sly,” and notes that the phrase is usually applied in “mild or jocular use.” It’s not a phrase used in anger, in other words, but the sort of thing you say when you discover you’ve been mildly deceived (“Oh, you sly boots. You snuck a seventeenth kitten into the house!”).

“Sly boots” is a very old phrase, defined (“a seeming silly, but subtle Fellow”) in Nathan Bailey’s 1721 Dictionary of Canting and Thieving Slang, and probably a good deal older. “Sly,” of course, means “cunning, clever or wily,” and comes from an Old Norse word meaning “crafty.” “Boots” is the interesting bit, originally, in the 17th century, used as slang for a servant in a hotel who cleaned the guests’ boots. It was also used to mean the most junior officer of a regiment or member of a club, the one most likely to be stuck with menial chores (“My chief resistance to discipline was at mess where I could not brook the duties of Boots..,” 1806). “Boots,” used as a synonym of “fellow,” also found its way into various humorous and colloquial phrases of the period, such as “smooth boots” (one who is adept at flattery and manipulation), “clumsy boots” and “lazy boots.” These phrases are rarely heard today, but I think there’s an excellent case for bringing back “smooth boots,” especially here in the US. It is, after all, an election year.