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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?

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    I can remember the term being used in elementary school in the late 50s. Eg: "He thought he was a big wheel, until he found out that squares don't roll." But there were many other uses with no geometrical connotations. (Mainly simple uses such as "Don't be a square" or "He's such a square.") My suspicion is that it comes from beatnik terminology. The original "etymology" may very well be lost. – Hot Licks Mar 17 '17 at 17:18
  • @HotLicks A lot older than that, according to etymonline, which says it's from a style of men’s shoes popular in the early 1700s. – Janus Bahs Jacquet Mar 17 '17 at 17:25
  • @JanusBahsJacquet - Yeah, it's certainly older than my introduction to it, since the term seemed to be old and well-established from the start -- no sense that it was an "in" term, other than the vague association with beatnik culture. Whether it's a logical extension of the 1700s origin or was reinvented is hard to say. (I'll note that your link associates it with jazz slang (from the 40s) for a 4-beat measure.) – Hot Licks Mar 17 '17 at 17:31
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    Even as a teenager in the 60s I thought square was dated 40s / 50s slang. – FumbleFingers Mar 17 '17 at 17:35
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    @AntonH - Ngram doesn't find "Be there or be square" until the 1960s, which roughly corresponds to my memories of the phrase. (Unfortunately, I can think of no good way to search for other representative uses of "square" in this sense.) – Hot Licks Mar 17 '17 at 21:41
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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:

SQUARE-TOES, subs. phr. (old.)—An old man (Grose) ; a FOGEY ["an old-fashioned or eccentric person"]; also OLD SQUARETOES. Hence SQUARE-TOED = formal, prim, testy. [Included citations:] 1771. SMOLLETT, Humph[rey] Clinker (1900)i. 65. He seems to have a reciprocal regard for old Squaretoes, whom he calls by the familiar name of Mathew. 1772. Bridges, Burlesque Homer, 23. Old Squaretoes ... Call'd silence; but he first with care Lifted his buttocks off his chair. 1860–3 THACKERAY, Roundabout Papers, xi. Have we not almost all learnt these expressions of old foozles, and uttered them ourselves when in the square-toed state. Ibid. (1862), Philip, xv. I have heard of an old squaretoes of sixty who learned very satisfactorily to dance.

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]:

Mr. Redwing, our Third Form master, was taken ill last year. You know we call him Square Toes, and he's been master of the Third ever since I remember: in fact, tradition runs that there never was a Third at St. Oliver's without Square Toes. He grew up with the building.

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):

SQUARE TOES, an old man; square-toed shoes were anciently worn in common, and long retained by old men.

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:

square n. 1. A full meal; a satisfying,filling meal. [Citation from 1894 omitted].] 2. A person scorned because he is not in the know or, esp., not cognizant of, wise to, or aware of the modern interests, activities, groups, fashions, or fads which the speaker considers vital; one who is or persists in being unworldly, unsophisticated, naive, old-fashioned, ignorant of current trends and interests, or unenlightened; a patron considered as a sucker; one easy to deceive, trick, or victimize because of his lack of worldly wisdom or knowledge of modern attitudes; one who accepts or believes without question all the pop. cultural, ethical, political, religious, and social rationalizations and mendacity; orig. and specif., one who is not aware of, or has no, or is probably incapable of feeling, sympathy toward or appreciation or understanding of bop, and, later, cool and far-out music, or of bop, cool, far-out, and beat attitudes and fashions; one who is not, and is incapable of being, hip; still later, one who has no sympathy for or understanding of teenage interests, esp. of rock-and-roll attitudes; one who accepts or likes commercial sentiment, sentimentality, and corn, esp. in music and entertainment; an uncritical spectator of entertainment and life, whose values, standards, and judgments are those popularly prevailing. 1943: "That G.L. {Guy Lombardo, orchestra leader} ... strictly a square." M. Shulman, Barefoot Boy with Cheek, 90. [Other citations omitted.]

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:

square ... 2 n jazz musicians by about 1925 A conventional person, esp. one with musical tastes not extending to jazz, swing, bop, etc. = CLYDE ["a person who does not appreciate the current music, culture, etc"] ... {the sense "conventional person, etc" is said to come fr the a jazz musician's and standard conductor's hand gesture that beats out regular and unsyncopated four-beat rhythm, the hand by doing so describing a square in the air}

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.

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The OED attests to square meaning

designating one who is out of touch with the ideas and conventions of a particular popular contemporary movement

from 1946, from music, in the Big Book of Swing by Bill Treadwell:

Square, not versed in Swing, puritanical.

The second reference is from 1950 in Julien Vedey's Band Leaders:

Consummate performer that Ellington is, he put these numbers over to the delight of all types of audience, young and old, sophisticated and ‘square’.

The Online Etymology Dictionary dates square in the sense of old-fashioned to 1944:

U.S. jazz slang, said to be from shape of a conductor's hand gestures in a regular four-beat rhythm.

As Janus Bahs Jacquet notes in a comment, the parallel term square-toes, referring to the same kind of person, had been in use in the late 18th century, in reference to a kind of shoe that had fallen out of fashion (thoughsince returned from time to time). There are no OED entries for square-toes for a "precise, formal, old-fashioned person" after 1889, however, so it is unclear if the earlier term influenced the later usage.

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@Choster has referred, quite rightly, to the OED adjectival use dating from their earliest example in 1946, which, like Etymoline, also connects the modern origins of square with jazz. That is sense 10d.

However, it is clear that square has had a broadly similar connotation for centuries.

Consider sense 11a - now obsolete- with its examples from circa 1590 - even employed by Sir Thomas More.

a. Precise, prim, solemn. Obs.

c1590 Sir T. More (Malone Soc.) 1425 Oh what formalitie, what square obseruance: liues in a little roome.

1601 B. Jonson Fountaine of Selfe-love ii. iii. 23 A serious, solempne, and supercilious face, ful of formall, and square gravitie.

1602 B. Jonson Poetaster iv. vi. 72 And all their square pretext of Grauity [is] A meere vaine Glory.

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