“Well, I be Puba on this here/The nigga from last year
Girbaud's hanging baggy/Tommy Hilfiger top gear”
-Grand Puba

Like a sonnet by Shakespeare, Byron, or Keats, this lyrical rhyme heralds one the greatest love stories ever told. After all, the tumultuous tale of what happened when Hilfiger met hip-hop can only be described as such. Set against the background of the early 1990s, the story of how the budding genre and the young label courted one another, fell in love, then fell apart has all the prerequisites of an iconic romance.

A fateful encounter.  A celebrated courtship. A deep commitment. A spectacular break up.

But before we get there, let’s start here: 1992—the moment the the quietly popular brand was publicly acknowledged by a hip-hop icon, Grand Puba. Less than thirty seconds into the languid first verse of Mary J. Blige’s hit single, “What’s the 411,” Puba uttered the above lyrics. The New Rochelle bred rapper was undoubtedly documenting the sartorial movement he saw happening all around him—young black and latino men remixing the preppy, well-priced alternative to Ralph Lauren. Puba’s lyrical nod ignited a groundswell of co-signs from hip-hop and pop culture acts like Snoop Dogg, Treach, TLC,  Aaliyah, and even Michael Jackson. The momentum didn’t just mark a feel-good era; it ushered in some of the most financially lucrative moments for the brand. In fact by the end of the decade, the company was grossing over a hundred million dollars a year.

Those glory days were not to last.  

By 1997 a mysterious rumor had taken hold that positioned the brand—and the man—as hating the very demographic that catapulted it to success. It took Hilfiger another decade to formally refute it on the Oprah Winfrey show, but by then, the thrill was gone. So too was the very public and very passionate embrace between Hilfiger and hip-hop—and with it the golden era of huge red and blue flags on huge celebs.

Now, nearly 25 years to the date of Puba’s iconic lyrics, the buzz is back. Drake, A$AP Rocky, and Nicki Minaj are just a few of the new school rappers paying homage to the old school cool of Hilfiger’s sailing jackets and oversize rugby shirts. But hip-hop stars looking back to the OG style of their forebears will always play out alongside the volatile relationship that Hilfiger had with the culture. From the early '90s when hip-hop found one of its first labels to partner up with, to the spectacular falling out that had rappers firing shots at Tommy Hilfiger in their lyrics, to read on for the epic story of love, hip-hop, and the billion dollar brand.

Written by Zandile BlayAdditional Reporting by Kadia Blagrove and Rae Ogbu.