Kid Cudi. Man on the Moon. The most hipster rapper I can think of. This guy is just awesome in so many different ways. Bright graphic t-shirts layered with beat up old leather jackets and plaid shirts. Crazy coloured socks combined with a classy suit and tie ensemble. He is the king of originality and mixing. He even wears the recognizable thick black framed, "hipster" glasses. He's always on top of his game, day-n-nite ;) .