Popsugar Celebrity Nostalgia Celebrity Couples in Matching Outfits | Pictures Two of a Kind: Matchy-Matchy Celebrity Couples April 1, 2015 by Laura Marie Meyers View On One Page Photo 13 of 14 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 13 Diddy and Jennifer Lopez For the MTV Music Awards in 1999, Jennifer Lopez and her then-boyfriend Diddy stuck to a similar style: shiny on top, leather on bottom. Previous Next Start Slideshow NostalgiaCelebrity Couples