This topic made me think of this website, which I love, because etymology (word evolution) is one of my all-time favorite subjects.

According to the dictionary, this connotation of the word square dates from 1944, and was used by the Jazz community to refer to the over-perfect conducting gestures that conductors in classical orchestras used.

"Old-fashioned." "Out-of-style."

...Boy, Square's not very square these days, is it?

I wish they'd go back to being square.