Watch Jay Z Debut Rocawear On The 1999 VMAs Red Carpet

Rebecca Romijn interviews rapper Jay-Z (in Rocawear) at the 1999 MTV Video Music Awards.
Photo: MTV

Talk about a Throwback Thursday! Back before Kanye West was selling out high fashion white tee collaborations, before A$AP Rocky was a fashion killa, there was a Brooklyn boy by the name of Jay Z (though, it had a hyphen then) building himself from a businessman into a “business, man” with a little streetwear line he dubbed Rocawear. Using Roc-A-Fella Records as the foundation, Mr. Shawn Carter and his long-time business partner Damon Dash decided they would spin the MC’s success into other creative business avenues. Before Hov was rocking Tom Ford, he was making a sartorial name for the R-O-C. And on what red carpet did Jay rep Rocawear in its debut year? The 1999 VMAs, DUH.

That’s right, folks. We dug up this clip of Rebecca Romijn interviewing a very young, very fresh-faced Mr. Carter for the 1999 VMA episode of House Of Style. In it, the flaxen-tressed glamazon of a model calls Jay out for not dressing up as much as he did for the MTV Movie Awards earlier that same year. He explains the clothes are all his own, “Rocawear, [it’ll] be in your stores soon.” ALERT: YOU’RE WATCHING VIDEO FROM A WORLD PRE-READILY AVAILABLE ROCAWEAR. And Rebecca points out that his kicks are Nikes to which he responds, “I don’t have the sneakers out yet, I’m working on that,” foreshadowing his 2003 S. Carter Collection for Reebok. *mind explodes* Hov defends his casual dress, saying that for the Movie Awards he wore a suit, following the adage, “When in Rome, do as the Romans do,” but his attitude toward the VMAs? “This is my world, so I do as I do.”

And boy, did he ever keep doing. Rocawear catapulted to one of the most visible and successful clothing brands of the early aughts, largely because Jay was down to wear it himself. He repped his Rocawear designs in music videos “Do It Again (Put Ya Hands Up),” “Anything,” “Izzo (H.O.V.A.),” “I Just Wanna Love U (Give It 2 Me),” “Change The Game,” and a GRIP of other public appearances. When it comes to VMA dude fashion, Jay-Z certainly wasn’t the first, but he was integral in the continued growth of men’s sartorial swag in the name of the Moonman. Catch even more VMA style discussion at 6 p.m. EST tonight on the VMA All Access Live Stream!



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