Square?

[Fletch]

'On the square' was (still is?) a Freemason's term relating to the compass and the square. A fellow freemason is said to be 'on the level' or 'on the square'

Did these terms pre-date general use in the vernacular? I know Masons were very central to white middle-class business culture in the 20s, certainly in the Midwest anyway - and you see the terms entering everyday speech in the early 30s, maybe earlier.

Were hepcats calling people "squares" perhaps a subtle dig at that fraternal, all-white-male, Main Street culture?

There's also the late 30s term "square from Delaware," which might just have been a cute rhyme or might have meant someplace small and slightly out-of-it.

People of German extraction used to be called "squareheads," both from the stereotypical buzz haircut (aka "Heinie") and (I think) the stereotype of Germans as strict, humorless and tightly wound.

Wallace Beery wears the Heinie in high style as an uptight, bullying German industrialist in Grand Hotel, 1932. Joan Crawford is his secretary-turned-personal property.