Who started it: Grand Puba
Circa: Early '90s

In 1989, Tommy Hilfiger was making $100 million in annual sales. During a random encounter at Kennedy Airport, Tommy Hilfiger noticed a group of hip-hop heads walking through the airport wearing his gear. His brother Andy, a former rocker, recognized Grand Puba and his crew and made introductions. Puba was a prominent 'Lo head, but also an early adopter of the Hilfiger brand. Although, it wasn't until Snoop rocked a Hilfiger rugby on SNL in 1994 that the brand really seized its hip-hop moment, endorsing up-and-comers like Aaliyah and Usher for commercials and magazine ads.