Jay-Z is super-duper famous. He's also probably on your list of top 5 rappers of all time. He's married to one of the most beautiful women in America, and probably has enough money to cover the surface of the earth. We're envious and salty, but we still love him just like everyone else (this excludes Beanie Sigel, but...well...*shrugs*). He rocked Yankee Stadium two nights in a row with Eminem last week and strengthened his already rock-solid status as an icon in the music world. Considering how much power he has, though, he isn't a very flashy dude. We find him to be pretty modest in dress (—definitely not in prose). However, with his own clothing line, Rocawear, and an assload of Hov stans around the world, he can't help but affect style trends. So we've decided to collect photos of Shawn Carter from back in 1989 until now. He's had some bad days and some good days, just like the rest of us. See for yourself: Check out his fashion picks in our Style History of Jay-Z.