I read an answer on another question where the answer was 'square' as opposed to 'not hip'. E.g. "Don't be a square!"
I have always been under the impression that the term came about because you are a 'square' if you're never 'a-round', implying that a 'square' person could just be aloof rather than solely 'not with it'.
But that may just be something my subconscious made up, I was not alive during the time period when this term was popular. Is my understanding of the etymology of the term square in this context incorrect?
Best Answer
J.S. Farmer & W.E. Henley, Slang and Its Analogues, volume 6 (1903) doesn't have an entry for square as a noun, but it does have one for the closely allied term square-toes:
Although squaretoes seems to have declined as a slang term during first half of the nineteenth century, it does show up occasionally in later Google Search books results. For example, An 1887 issue of Puck includes the script of a vignette called "Moral Dialogue" set in a school called "Professor Squaretoe's Academy," directed by the hypocritically pious Professor Squaretoe. And in a story in The Boy's Own Annual, volume 34 (1911), a schoolboy character says the following to a companion [combined snippets]:
Both of these sources are from British sources, however, and it may be that "old squaretoes" was extinct in North America long before it vanished from England.
Farmer & Henley's reference to Grose is probably to this entry in Francis Grose, A Classical Dictionary of the Vulgar Tongue (1785):
It is easy to see how square-toes might be shortened to square while retaining its ancient sense of fogeydom. Still, Harold Wentworth & Stuart Flexner, Dictionary of American Slang, first edition (1960) seems to view square in the sense of fogey as an invention of the 1940s:
That is the most comprehensive and accurate definition of square I have ever seen; but I'm not persuaded by it that the term has no connection to old square-toes.
Robert Chapman & Barbara Kipfer, Dictionary of American Slang, third edition (1995) pushes the origin of this sense of square back to the 1920s, but still doesn't see a connection to the older term:
The similarity of the jazz-era meaning of square to the eighteenth- and nineteenth-century meaning of square-toes may be entirely coincidental. But I think that the coincidence bears noticing.