Last year, as a bit of an upset from history, it was a dude who created one of the most viral moments on the red carpet of the Met Gala. And it wasn’t necessarily because of his look. When Diddy took to the steps of the Metropolitan Museum of Art on 2017’s ‘First Monday in May’ for photos, he decided take a seat—to recline even—presumably letting the focus go to Cassie, his date. He may have have been there with Cassie to celebrate the work of Comme des Garçons designer Rei Kawakubo, but, as Diddy does, he inevitably became the center of attention and a meme in his own right.

“I was getting tired so I laid down on the stairs!!!” he wrote on Twitter later. Tired of what? Maybe it was just Met Gala prep, sure. But also possibly tired of beating a trail through history as a fusion between hip hop and high fashion. A trail through which the likes of Kanye West, Nicki Minaj and A$AP Rocky would follow. A trail that even Virgil Abloh, Cardi B and A$AP Ferg would take up after them. But, in many ways, Diddy was the first.

In a recent story and social video entitled “Why Rappers Are Fashion’s New Royalty,” Business of Fashion says that “the fashion industry has woken up to the marketing power of America’s greatest cultural export,” that export being hip hop. Specifically, the video cited Cardi B sitting next to Anna Wintour, a prestigious seat at a fashion show, at the Alexander Wang show in February as an “unlikely front row pairing.” For them it was an indication that the industry had changed a stance on trying to keep connections with hip hop at a minimum. But really, it was just the latest step in a 19 year process started by Diddy.

Cardi B was not the first rapper to sit beside Anna Wintour at a fashion show. She wasn’t even the first female rapper. In 2012 NIcki Minaj rapped about “sitting with Anna” on her track “Come On A Cone”, likely referencing sitting beside the editor at the Carolina Herrera and Oscar de la Renta shows in 2011. But even before that, Diddy, then Puff Daddy, was taken to the Christian Dior Haute Couture show by the power player all the way back in 1999.

1999 was Diddy’s breakout year in high fashion. Then trying to drum up support, credibility and knowledge for his Sean John label (launched in 1998), he pulled in as many power players as he could. Jeffrey Tweedy, who had logged time at brands like Ralph Lauren and Hugo Boss, would be first to come on board. The PR guy? Paul Wilmot, who had been at Calvin Klein and would go on to found his own agency later. Informal advisors? Anna Wintour and Tommy Hilfiger. Wintour would go on to cosign Diddy’s fashion bid in a big way.

As chronicled in 2000’s BBC1 documentary “Boss Women,” during the Fall 1999 couture shows, Anna Wintour arranged for Diddy to be shot by Annie Leibovitz in a Vogue spread set in Paris. While the rapper and mogul was the star, the editorial also featured (fellow) fashion icons like of Kate Moss, John Galliano and Karl Lagerfeld. During the process of the shooting, Wintour got publicly cozy to Diddy, inviting him to the Dior show to sit beside her (Andre Leon Talley sat on her other side) and explained how the industry worked. In the documentary, the narrator explained the benefit to her.

“Realizing Puff Daddy’s potential to add street cred to haute couture, Anna signed him up for an exclusive Vogue feature to be shot in Paris,” the narrator says. Diddy would go on to incorporate the editor’s industry know-how with his own marketing and branding expertise, logging a series of firsts in fashion history.

In 2017, in a story about Christopher Bailey’s tenure at Burberry, Vogue pointed to the brand as being an early adopter in the livestream movement. While it’s true that the brand has been amongst the firsts to digitize fashion in major ways, as far as streaming a live runway show, Puffy was about 8 years ahead with his with his million dollar Sean John show in 2001. He would also go on to be he first black man to win the CFDA Menswear Designer of the Year award in 2004 with the brand. The only other black man to also win the award to date? Maxwell Osborne, who had been on the Sean John team during Diddy’s win. Osbourne would go on to co-found Public School, the brand that propelled him to his own CFDA win. That award and the Wintour association would distinguish the mogul from others like Jay-Z and Russell Simmons who were making similar attempts as being endorsed by the industry at the highest echelons.

Diddy’s legacy, in fashion in particular, is long lasting. As one figure he not only logged a series of firsts for hip hop and black people in fashion but also began a long lasting campaign that continues today pushing categories like ‘urban wear’ and streetwear into high fashion territory. But he also nurtured a generation of talent. In addition to Dao-Yi Chow and Osborne, other Sean John alum like Christopher Bevans, who worked for a time on the brand’s high-end denim line, are finding industry success.

Sean John is not the heavy-hitting name it was, now two decades into business. Even though it has a longstanding partnership deal with Macy's and was acquired by Global Brands (with Diddy still holding shares, naturally) back in 2016, it trudges on. This month, as a part of the 20 year anniversary and in celebration of the musician-adjacent roots of the brand, it has released a capsule of T-shirts printed with photos of artists like Jimi Hendrix, Aaliyah and Marvin Gaye. Diddy himself, the consummate mogul, is hardly one to focus on a single venture or investment. He recently paid $21.1 million for a highly-sought-after Kerry James Marshall painting.

With some many irons in the fire, who can truly say when or what Diddy’s next fashion venture will be. A better prediction? Maybe in 20 years Diddy will be reclining on the steps of the Met for his own fashion retrospective.

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Tags: met-gala, nyfw, sean-john, diddy