I would assume that it's the kind of hat that makes you look like a happy-go-lucky, carefree bastard. Wacky, or at the very least goofy, while still posessing at least some semblance of style, it tells the observer. "Hey, YOU might think I look like a retard, but I don't, so fuck you with a chicken."
It is the absolute counterpart to the top hat.
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