In the early '90s, Tommy Hilfiger dominated the wardrobes of hip-hop's biggest stars. Grand Puba, Snoop Dogg, Q-Tip, and more co-signed the preppy brand. Others, like Treach from Naughty by Nature and Raekwon, even walked in fashion shows and appeared in campaigns for the brand's sportier offshoot, Tommy Jeans.

At ComplexCon 2018, we wanted to remember that era in hip-hop style and explore the brand's history with the genre's elite. So we gathered Tommy himself, Grand Puba, Lewis Hamiltion, and Tommy's brother Andy for a rare conversation. During the talk, Tommy discussed the iconic ad campaigns that featured Aaliyah and explained what they meant to him and the brand at the time. "For me, it was like unlocking the door to music, fashion, and celebrity advertising and embracing the culture as a designer and allowing the public to realize that we were going to break the rules in fashion," he said. "So we started making clothes way oversized. We started making logos way oversized. We started listening to the youth." 

He also addressed rumors of racism that plagued Tommy Hilfiger in 1996. "It hurt my heart because I didn't want people to really believe that," he said. "That rumor is untrue. It's a total lie." 

Grand Puba, an early supporter, also explained what drew him to the brand. "In hip-hop, you always try to be innovative and try to do somethin' that the next man ain't doing."

Watch our Hilfiger & Hip-Hop ComplexCon(versation) above.