25. Kris Kross with the backwards clothes in "Jump."
Moms was still buying normal-fitting clothes when turning 'fits backwards became a trend, it was hard for most of us to make the jeans cooperate. But you know we tried, as did every kid in America-and adults took notice. The trend was absurd, but that was the purpose. The look ultimately helped Kris Kross blow up and go multi-platinum.