Plimsoll Dickhead Share definition Flag A male who wears a combination of Plimsoll's tight jeans and a v-neck. They commonly have rich parents, massive egos and listen to Tinnie Tempha. Look at that Plimsoll dickhead, did he put his sisters t-shirt on by accident? Plimsoll Dickhead by badman3000 December 3, 2011 Get the Plimsoll Dickhead mug.