Last week, the internet basked in the reuniting of Jennifer Lopez and Ben Affleck. Then, P. Diddy (“Sean Combs”) threw his hat into the ring. He posted a throwback paparazzi shot of the duo, presumably taken while they were dating between 1999 and 2001. In the image, the rapper wears a gray Sean Jean sweatsuit with white sneakers while holding a baseball cap and a newspaper, while Lopez wears a white cushy turtleneck, her signature hoops, bootcut faded jeans, and metallic gold sandals with a stack of magazines under her arm. At the height of the second coming of Bennifer, Diddy’s caption was simple: “#tbt”.
While Affleck and Lopez have curiously and deliciously opposite tastes in clothing, Diddy and Lopez are united in their love of luxury. Their relationship came during career highs for the both of them: Diddy had an album out, and Lopez was just segueing into the world of acting from pop stardom. Similarly, their looks were in sync. After all, Diddy has always been one of the most well-manicured men in the music world. In the studio, he’d wear a pair of overalls, a big fat gold watch, and a diamond-slathered pinky ring. On the red carpet in 1997, at the Soul Train Awards, he dressed up in a three-piece white suit but with an iced-out Jesus necklace in lieu of a tie.
Even before J.Lo, Diddy liked to have fun in fashion, as evidenced by his appearance in the October 1999 issue of Vogue, where he was photographed by Annie Leibovitz alongside Kate Moss. Back then, Diddy was known as “Puff Daddy” (he’d later go through several moniker changes) and was heading to Paris Fashion Week. The article, written by Plum Sykes, chronicled the rush and glitz of the artist’s time in Paris, down to the tally of hats he had in his hotel suite and the number of bodyguards on his team (26 hats, four bodyguards). In the piece, Jean Paul Gaultier said of Diddy, “He’s a little bit like Liberace. I think. All those rings.”
Just before they joined forces, Lopez released her hit debut album On the 6. She was developing her style identity, which vacillated between navel-baring hottie and Old Hollywood bombshell. Off-duty at LAX in 1999, she was spotted in a nubby turtleneck, shades, and the most glamorously casual piece of all, a pair of white jeans. On the red carpet, she’d wear a mini tube dress that looked like it was dipped in gold at the Grammy Awards in 1999, or she’d evoke Grace Kelly in a strapless black gown at the Vanity Fair Oscars party. Lopez was coming into her sultry, magnetic own.
When Diddy and J.Lo got together in September of 1999, their coordinating looks were unforgettable. They attended the 1999 MTV Music Video Awards hand-in-hand. Lopez wore a shimmering fringed halter top, a midi-skirt with a high slit, and knee-high leather boots. She clutched her French manicured hand around Diddy’s who was wearing a blinding diamond bracelet, semi-sheer black cut-off sleeve shirt, leather pants, and three massive chains with fist-size crosses. The couple artfully mirrored each other. At the after-party, they both wore white: Lopez in a glinting tweed tube dress and Diddy in a white tank with the same leather pants.
The pinnacle of this union was at the 2000 Grammy Awards when J.Lo wore that tropical Versace dress. (Yes, the one that spawned the birth of Google images.) At her side was Diddy, wearing a silvery, sheeny suit with rimless sunglasses. It’s rare to see a couple that is so fashionably on each other’s level. Diddy, of course, still seems to agree.