When: 1994-1998

When Snoop Lion (formerly, Dogg) wore a red, white, and blue Tommy Hilfiger rugby on Saturday Night Live in 1994, the American designer went from preppy staples to being hip-hop's favorite designer. Marked by the signature red, white and blue logo, Tommy was the definition of casual luxury. The brand was featured in countless music videos and photo shoots and Tommy even enlisted hip-hop personalities like Aaliyah to star in his ad campaigns. Tommy was so popular that designer imposter versions circulated at thrift shops and swap meets. The fad came to an abrupt end in the late '90s when a rumor began to circulate that Hilfiger was racist, telling Oprah that he didn't want rappers to wear his threads. Despite the fact that the rumor was proven false by both the designer and Oprah, the damage was done and no one has felt quite comfortable ever since in their Tommy overalls. "I looked at the rap community like street kids wanting their own brand. But now I look at that period with the rappers in the '90s as a trend of the moment. What it taught me was never to follow a trend, because trends move on," Tommy said years later. Interestingly, Tommy's son, Rich Hilfiger (a.k.a. Ricky Hil) is a budding rapper. 

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