Typically refers to a guy who dresses in a completely inappropriate manner for a given social situation. In truth, a riddler cannot be defined, and is only fully understood once he is seen in person.
"Look at this fucking Riddler. Who the fuck wears white driving loafers, blue jeans, a tuxedo shirt, cardigan, and a god damn Yankees cap to a dive bar!?"
by Are2Dee2 November 22, 2010