Why do we (or did we) use the word "square" to mean "uncool"?

Answer 1

Its like the old saying goes you can't fit a square peg into a round hole. So the term square was used to describe someone different or unusual because they didn't fit in.

Answer 2

It means you were living inside the box of traditional thoughts and values. If you were what they considered open minded, you were thinking outside of the box, IE: not square. Unfortunately, far too many people got caught up in that psyco babble and abandoned their values and self esteem in order to be accepted by those of lower values. Go figure...

Answer 3

Because square does not rol, with the flow