I read this on The Oatmeal:

Hey, he is clapping along to the music! How quaint! I should too. I would not want to look like a square!

Another one:

You Won't Look Like a Square With B-Side's Cubic, Steam-Punk Jewelry

(Emphasis added.) Now, what does it mean by looking like a square? Amazingly, Google doesn't know what that means.

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    Great Oatmeal btw; so true :) – Jonik Sep 19 '10 at 17:11

A Google search for define:square gives me as one meaning

a formal and conservative person with old-fashioned views

which is what "square" means in your example.

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    +1 for your answer, and thank you for the good chuckle :) – e.James Sep 18 '10 at 22:31
  • AKA "stick in the mud," a person who is no fun. – moioci Sep 21 '10 at 6:47

It began in the 1960's (I believe, or possibly earlier) and is the opposite of being "hip" or "with it". There is a definite negative connotation which is missing from Ex-user's Google definition.

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  • But later it became hip to be square ;) – mplungjan Feb 7 '11 at 7:30

The antithesis of "hip". The Wikipedia article about it gets a bit rambling but captures the essentials.

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