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We found the answer to your question on an excellent Q&A site called The Straight Dope. As it turns out, the dunce cap comes from a 13th-century philosopher named John Duns Scotus, who, not surpisingly, was born in Duns, Scotland. This well-respected but terribly oblique scholar felt that conical hats actually increased learning potential. Here's the theory -- knowledge is centralized at the apex and then funneled down into the mind of the wearer. Scotus was an inveterate hair-splitter and came up with terms like "haecceitas," or "thisness." He was widely praised in his day, but eventually fell out of intellectual favor. His "duns cap" was a pretty obvious target of derision and came to symbolize stupidity.
So the logic behind the dunce cap is that it makes slow pupils learn better, but it was later used to humiliate the wearer and motivate students to try harder.
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