[1][2][3] This sense of the word "square" originated with the American jazz community in the 1940s in reference to people out of touch with musical trends.
[1] Older senses of the term square, referring positively to someone or something honest and upstanding, date back to the 16th century.
[3][4] The English word square dates to the 13th century and derives from the Old French esquarre.
[6] A West Country variant on the phrase, "fairs pears", bears the same meaning and was first traced by Cecil Sharp in 1903 when visiting his friend (and lyrics editor) Charles Marson in Hambridge, South Somerset.
In contemporary language, U.S. branches of the military refer to "squared away" to describe things that are ordered.