This is a kind of canvas hat that guys wear with the brim pulled down. It is so-called because the wearer knows it looks bad; yet wears it anyway as an expression of nonchalant contempt for convention. In effect, sartorially declaring "Kiss my ass!"
My boyfriend dresses really nice; but occasionally spoils the effect by wearing what guys call his kiss my ass hat.
by evil pop tart December 24, 2009