When: 1993-2006

For many unfamiliar to the many nuances of style in rap, the baggy jean is the definitive hip-hop look. For good or bad, baggy jeans became the de facto look for every rapper from the early '90s to just a few years ago. Rappers and fans alike began wearing their jeans several sizes too big. Sagging? No problem! Just rock a belt or better yet, let your boxers show. Many experts believe that sagging originated in prison, where inmates weren't allowed to wear belts. Mainstream America marked the silhouette as a sign of delinquency. Schools around the nation tried to combat the power of the sag with mandatory uniforms and several states like Virginia and Louisiana actually tried to outlaw the look. In 2007, the New York Times wrote, "Not since the zoot suit [of the 1930s] has a style been greeted with such strong disapproval."