Gazoooo On The Loose.. ‘I Felt Pretty’: For His 50th Birthday, Diddy Reflected on Life as Fashion’s Bad Boy

As someone who’s spent her entire working life in the fashion and music industries (over two decades and ongoing), it remains challenging for me to think of Sean Combs as anything but “Puffy.” You see, as a Gen-Xer, I remember well his evolution from upstart promoter to music exec to entertainment juggernaut…while unfortunately, my mind only evolved to “Diddy.”

Sean “Love” Combs? I simply can’t.

But for Diddy’s decades of success in entertainment, less discussed is his impact upon fashion. As the mogul turned 50 this week, Voguecommemorated the occasion with another anniversary: It’s been 20 years since “Puffy Takes Paris,” the October 1999 editorial by Annie Leibovitz that paired the artist formerly known as “Puff Daddy” with supermodel Kate Moss for a French Fashion-Week-themed pictorial. As Vogue notes, it was “the height of the ’90s ‘bad boy’ phenomenon,” and Puffy was its CEO, chief brand ambassador and one of its cultural catalysts. But as he now reveals while dropping a series of reflective gems for the magazine, the bad boy wasn’t too cool to be completely in awe of the experience of posing for Vogue.

The inspiration of fashion [viewed] through hip-hop culture becoming mainstream globally on fashion’s biggest runways and in fashion’s biggest magazine. I understood that. I knew something big was going on; I wasn’t jaded. I’m not going to lie: I was like a schoolgirl. I was so happy to be involved. I was like, ‘There are no men in Vogue, [but] I’m in Vogue.’ I felt pretty.

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