45. Sean John
Casual sportswear from Europe had been heavy in the streets for a minute by the time Puff Daddy ventured into clothing, but when Sean John dropped in 1998 hip-hop could finally stop appropriating its style cues from the Continent and cop from the home country. Sean John was an immediate hit in the streets and with critics, and made velour suits acceptable to rock outside of the home again. It's initial success was so influential that, heading into the early 2000s, Sean John started cleaning up when it came to awards and top media coverage.