Welcome back, James...........

When was it decided, why and by whom, that 'square' meant conservative? ie. Years ago if someone was square, they were maintstream, conservative, etc. And of course, then there's the saying, 'think outside the square', suggesting that if you want to do something different, break the mould, etc. you have to think outside a square.

My 'The American Thesaurus of Slang', circa 1956, certainly gives the conservative version and likens it to 'trite' or 'corny'.

Welcome back, James. You were missed.