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I'd personally think "יש לו ראש מרובע" means literally that his head looks like a square, I'm not familiar with it being an expression or fixed phrase. However, to call someone "מרובע" used to be slang for "nerd".
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I've also often heard מרובע and sometimes also ראש מרובע in the sense of straight or in the box. But it's a bit old now, these days I don't think it is used much unless somebody has a square-shaped head, or, more likely, an object has a square top or tip (the tip of a drill, for example, is referred to as ראש).
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I know מרובע as someone who is very "straight" or "in the box". I've mainly heard about square heads used as a joke about Georgians (from the country of Georgia).
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In Québec, "tête carrée" is a casual, humorous way of designating an English speaker.
".הוא ראש מרובע"
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In Russian it means that someone can't think straight because of a headache or thinking/worrying too much
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In spanish, "cabeza cuadrada" is an adjective usually for people a bit tough, strict, like they said "in the box". Either intelligent, stupid or normal.