Most stylish moment: Signing an endorsement deal with Tommy Hilfiger before you even knew who that was

While most other rappers were experimenting with making super-casual practical gear—sportswear (Starter, Columbia) workwear (Carhartt, Dickies) and fatigues—fashionable, Puba went in the other direction, taking his fashion cues from Ivy League preps and New York's legendary Lo-Life crew. But rather than only rocking the man on the horse, when Puba went solo with 1992's Reel to Reel, he wore extra-large pieces from another colorful, preppy American line, Tommy Hilfiger. Around the same time, a chance meeting between the designer and Puba led to an endorsement deal, which helped make Hilfiger a hip-hop go-to throughout the '90s. On top of that, Puba single-handedly blew up Girbaud jeans, and helped make backpack a fashion item.