Sean John P. Diddy Hip Hop Cool Streetwear Duo Fashion Print Ad 1999 1990s

Sean John wants hip-hop swagger to be taken seriously as high style, and this 1999 ad makes the case with rapper P. Diddy and a friend wrapped in a loose shoulder hug. Both wear black velour zip jackets, chunky chains and bling, while a finger points straight at the signature stitched on the chest. The "Future of Fashion" line sums up the era, when hip-hop stars were launching their own clothing labels and changing what cool looked like. It is a sharp black-and-white snapshot of late-90s streetwear.

• Cursive logo and a phone number anchor the page
• City list names New York, Los Angeles, London, Tokyo and Paris
• Diamond watches and a dog-tag pendant add flash
• Fun pick for music memorabilia and street-culture collectors
• Measures approximately: 8" x 11"