Boat dad
Guy who wears loafers without shoes with khakis with a polo all the time. He may also have a wife that spends all his money shopping at Talbots or Charter Club. Typically he is a republican. He may or may not have a yacht, but feels the need to project that he does at all times. Usually these actions are born out of a deep sense of both inferiority and a need for self importance.
Guy 1: I wish that guy would get that smug look off his face, who does he think he is with those expensive khakis and boat shoes? We're not on a dock here!

Guy 2: I heard he lost all his money in a bad business deal. He's broke! He's a real boat dad.