17. Kris Kross
Even though their whole style was a gimmick, it was one that worked. Whether you clowned or copied their backwards clothes, it was an undeniable moment in the annals of hip-hop style. It wasn't just the fact that they wore their clothes backwards that was interesting, it's that they were wearing awesome stuff anyway. We're talking baseball, hockey, and basketball jerseys, carpenter jeans, Timberlands, and enough Starter gear to make a nostalgic hipster foam at the mouth.