Who started it: Kriss Kross
In the pre-Internet days, standing out from the crowd was important to get your work noticed. No one was reblogging your shit our retweeting your links. One way to do that? Dress in a unique way. The kids from Kriss Kross got the idea of turning their clothes backwards, and when their music videos started hitting the airwaves, plenty of old heads thought it was corny, while younger kids of the '90s thought it was the coolest shit they had ever seen. Of course, much like Kriss Kross' rap career, this trend was short-lived.