it's exactly what you think. some smarmy douche of a dude who has a polo shirt tucked into white pants, penny loafers, sweater around the neck, and is part of a yacht club... you probably hate this person just by looking at them. think carlton from fresh prince of bel air. saying this to someones face is awesome because they don't know the meaning and you have just massively insulted their dignity.
"hey look at that fucking cheddar beakley" (everyone laughs)