Jennifer Lopez

Where: 42nd Grammy Awards

When: February 2000

Complex says: Oh, the infamous Versace green dress. Jenny from the block wore the plunging dress to the Grammys that year and, guaranteed, had all the dudes hating on P. Diddy. The iconic dress—it was displayed at the Grammy Museum in Los Angeles and a copy of the dress was shown in Vienna to celebrate 50 years of history of Italian fashion—definitely made Versace a household name. So even though J.Lo isn't really hip-hop, this one's just too good to leave out.