In 1992, Grand Puba appeared on an episode of Yo! MTV Raps  with Mary J. Blige to perform their song “What’s the 411?” Puba was dressed in a white Fila visor, a pair of Nike Revaderchi sneakers, and a color-blocked Polo Ralph Lauren Alpine rugby shirt tucked at the belt loop of his Girbaud denim shorts. At the time, these were the hottest brands in hip-hop. But, in the lyrics of the song, Puba would introduce a designer label that was new to the rap community: Tommy Hilfiger.

Well I be Puba on this here/The n***a from last year/Girbauds hanging baggy/Tommy Hilfiger top gear

Born in Elmira, New York, Tommy Hilfiger got his start in fashion when he and two friends opened a small store called People’s Place in his hometown in 1969. People’s Place sold mostly bell-bottom jeans, rock n’ roll posters, records, and rolling papers. The shop was a success and Hilfiger launched several other locations. But by 1979, People’s Place had gone bankrupt.

Seven years later, Hilfiger founded his eponymous label. “I knew exactly what I wanted to do—I wanted to build some kind of lifestyle brand that was preppy and cool,” Hilfiger explained to The Guardian. The label Tommy Hilfiger, which included classic collegiate styles like polo shirts and chinos, wasn’t initially intended for rappers. But the bright graphics and colors spoke to many rappers’ bold sensibility and drew them to the brand.

Hilfiger and his brother Andy took notice of the unlikely endorsement and started building relationships with hip-hop artists. Soon, they were dressing everyone from Raekwon to TLC, placing them in ad campaigns and inviting them to walk in runway shows for the brand’s sportier offshoot, Tommy Jeans. But in December 1996, a rumor surfaced online that Hilfiger had appeared on The Oprah Winfrey Show and made racist remarks about the people purchasing his clothing. Hilfiger denied the hearsay, but ultimately, the controversy hurt his label and his relationship to rap music.

Decades after Hilfiger became the hottest brand in hip-hop, key players in the industry at the time reflect on Tommy Hilfiger’s legacy with rap culture, how it fell apart, and where the brand is now.