Tommy Hilfiger and style of the '90s are almost synonymous. By looking back to classic American preppiness and updating the aesthetic with modern reinterpretations, the brand struck a chord with everyone concerned with style in the '90s. From hip hop heads to Wall Street bros, everyone had some Tommy in their style arsenal. He grabbed everyone's attention in 1985 when he posted a billboard claiming that he was in the same class as Ralph Lauren, Calvin Klein, and Perry Ellis. People had their doubts, but by the end of the '90s, Tommy reigned supreme. And when Aaliyah rocked the Tommy sports bra, underwear, and denim? Game over.