15. Andre 3000 with the Atlanta Braves jersey in "Player's Ball."
Before 3 Stacks hooked up with Erykah Badu or started wearing football equipment, he was just a kid from Atlanta. As evidenced by his indignant acceptance speech for Best New Artist at the 1995 Source Awards, he must have felt Atlanta was getting shunned by the Yankees up north and was determined to put on for his city. Thus the Braves jersey isn't just the moment of Andre's fashion sense being down to Earth (as opposed to being down to Mars), but a significant moment of hometown pride.