"Hip" is a slang word for "modern" and "square" for "boring" so the title means "It's modern to be boring". The song is about a guy who was rather rebellious in the past, wore his hair long and it's implied that he was into partying, alcohol and perhaps other substances as well. Now he has become calmer and conforms more to societies' expectations. He has changed his outer appearance and strives for a  healthy lifestyle. Those changes are not so much a matter of growing up but rather of following the zeitgeist. The lyrics are pretty ironic but there is a grain of truth in it. 

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