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.

Swim if you can.

Dear Word Detective: I am doing a report on the word “school.” Can you please tell me what its origins are and when the word was first used. Which came first — a school of fish or a school for learning and education? Why is a group of fish called a “school” anyway? — Alyssa.

Oh boy, a school question. I usually don’t answer research questions from students on principle, the principle being that I spent many years not doing my own homework, so why in the world should I now do theirs? In this case, however, the question has a delightful recursive quality, and the answer is not what most people (possibly including your teacher) expect, so we’ll give it a shot. Besides, I must admit that I enjoy participating in the educational process from a safe distance. It’s like watching the guy next door shovel his walk from the warmth of your own living room. In fact, I think I’ll have a tasty stick of gum while I write.

I’ve never been good at keeping a secret, so I’ll cut to the chase right away. The “school” one attends in hopes of having a well-rounded education and success in life is an entirely different word than the “school” fish join in hopes of whatever fish hope. This probably seems strange and perhaps a bit of a letdown, considering that fish in “schools” display a regimentation that is the envy of every human teacher out there, but they are indeed two different words, with two different origins.

The “school” meaning “place of instruction” comes from the Latin “scola,” itself derived from the Greek “skhole,” meaning “lecture or discussion.” Interestingly, that Greek “skhole” originally meant “leisure, free time.” It then developed to mean “time used for intellectual discussion,” then to mean the discussions themselves, and finally to mean the place where such discussions were conducted, what today we would recognize as a “school.” We inherited “school” from the Old English form “scol,” and almost immediately began using it in the figurative sense of “an environment which teaches through experience” as in the “school of disappointment,” or the 20th century variant “school of hard knocks,” meaning a period of deprivation and abuse. By the early 17th century we were also using “school” in the figurative sense of “group of people who share agreement on a subject” (as in “school of thought”). And “school,” as you’ve probably guessed, also gave us “scholar,” “scholastic” and similar derivatives.

Meanwhile, elsewhere in English, we were adopting the Middle Dutch word “schole,” which meant “group of fish or other animals.” Although originally it was possible to speak of a “school” of pheasants, for example, in modern usage this “school” is applied only to fish swimming together.

Unblinking.

Dear Word Detective: When I was growing up in rural Nova Scotia, my mother often used a word to describe my sister or myself when we were in irritable moods. I have never known how to spell this word, but it sounds like “owly,” as in “Your sister’s in an owly mood” or “Why are you so owly?” Anything you could tell me about this word would be gratefully appreciated! — Lady G.

That’s a good question. Incidentally, of all the possible introductory biographical clauses one could encounter in such a question, “when I was growing up in Nova Scotia” ranks as one of the most evocative and romantic. It’s right up there with “growing up in the Cotswolds” and “as a child on the moors of Cornwall,” and certainly beats my “when I was growing up in suburban Connecticut.” Technically, I suppose I can claim to have grown up in New England, but that’s only sightly better, and whatever faint cachet it confers collapses completely when folks discover that I don’t like seafood.

Speaking of preconceptions, it’s interesting how many people write me about an odd word or phrase their parents or grandparents used, while themselves clearly harboring the suspicion that Granny might have simply invented the term. Yet this is almost never the case. Even the strangest figures of speech heard dimly in one’s long-lost childhood usually turn out to have a reasonable explanation.

Such is the case with “owly,” which is indeed how it’s spelled. Since at least the mid-19th century, “owly” has been a colloquial term meaning “cranky, cross, angry or fretful.” It’s considered a regional usage, found largely in eastern Canada and the Upper Midwest of the US.

The Oxford English Dictionary lists “owly” first as a synonym of “owlish,” meaning, literally, “resembling an owl,” but usually applied to people who exhibit an unblinking, calm (but often critical) gaze, similar to that of a wide-eyed owl (”The little man with his most owlish air of wisdom,” I. Zangwill, 1895).

“Owly” as a synonym for “cranky” or “irritable” appears to draw on another aspect of the owl’s appearance. Many species of owl have tufts of feathers above their eyes, making the bird resemble a little man with his brow furrowed in disapproval and annoyance. Coupled with the owl’s intense, piercing stare, you have a perfect visual metaphor for someone in a persistently implacable bad mood.

Bang on the mark.

Dear Word Detective: I have been teaching marksmanship for the past five years and I have been a pistol shooter for ten years now. One day, I was asked by a student about the origin of the word “marksmanship.” I am not really sure about my answer but I told them that perhaps the word is derived from the Mark’s rifle in the same manner that the word “sniper” is derived from the word “snipe” (a type of small bird found in India). — Jack Palanca.

That is a darn good question. I didn’t have much luck tracking down your reference to “Mark’s rifle,” but it is true that the word “sniper,” meaning a military sharpshooter, comes from the “snipe,” a small bird found in marshlands in Europe, Asia and New Zealand. Snipe are, apparently, quite hard for hunters to hit, leading to the verb “to snipe,” meaning to shoot very precisely at an animal or person. “Sniping” also usually consists of a single shot, which gave us the figurative sense of “to snipe” meaning “to verbally attack sharply and quickly,” often with a single sly gibe (”Although adult factions may have made peace with each other, their children on the way to school may continue sniping at each other for generations,” 1959). “Snipe” as a noun also became a derogatory term, leading to “guttersnipe,” originally a Wall Street epithet for shady stock traders who conducted business on street corners.

“Marksman,” meaning an accomplished sharpshooter, rests on a special meaning of the common English word “mark.” The original meaning of “mark” when it first appeared in English, based on Germanic roots, was “boundary or limit.” In Old English, “mark” had taken on the logical sense of “an object or sign denoting a boundary,” which underlies many of our modern uses of “mark” to mean a notation or sign signifying something.

One of the early uses of “mark” in English, around the late 13th century, was to mean “target or other object set up to be shot at by an archer.” This was extended to mean any target shot at, and even used figuratively to mean the “target” of a scheme or ruse (as criminals today still refer to the victim of a swindle as “the mark”).

Oddly enough, one meaning of “marksman,” when it first appeared in the early 17th century, was “a person regarded as a victim or target.” But that meaning quickly gave way to our modern usage meaning “a person skilled in shooting.” So whatever the story of “Mark’s rifle,” the word “marksman” simply means one who is skilled at hitting the “mark” or target.