Year It Dropped: 2008

Disney has long figured into the graphic realm of the streetwear world. After all, we're all kids at heart right? Remember how ubiquitous Mickey Mouse clothes were in the '80s? What's surprising about this collaboration is that Disney was down to officially endorse it. Bobby Hundreds recounted the experience and intellectual hoops he had to jump through in order to make it happen, and the fact that it did showed that streetwear had become mainstream. Did The Hundreds sell out? No, not at all, it was done in small runs (200 of each character) and the graphics, reinterpretations of Peter Pan's Lost Boys as California juvenile delinquents, looked cool. Even the accompanying caps meant to pay homage to Peter Pan's feathered hat and Captain Hook were covetable too. But it still marked a shift from streetwear as a rebellious movement to legitimate business entity—and growing up sucks.