For this UnexpectedCrushTuesday, we jump from JLO and Ben Affleck’s opposite looks to JLO and Diddy’s elevated tastes
, 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”.
Even before J.Lo, Diddy liked to have fun in fashion, as evidenced by his appearance in the October 1999 issue of, where he was photographed by Annie Leibovitz alongside Kate Moss. Back then, Diddy was known as “Puff Daddy” 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 .
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.
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