Popsugar Fashion Nostalgia Jennifer Aniston and Brad Pitt's Best Fashion Moments Brad and Jen's Most Stylish Moments Prove They Should Have Another Reunion — For Fashion's Sake September 23, 2020 by Sarah Wasilak View On One Page Photo 3 of 23 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 3 Jen's Elegant Red Prada Gown and Satin Shoulder Bag Stole the Show at the Emmys in 2000 Brad kept it simple, letting his lady shine — she was nominated that year for outstanding supporting actress in a comedy (Friends), after all. Previous Next Start Slideshow Jennifer AnistonBrad PittNostalgiaCelebrity CouplesRed CarpetFall FashionThe '90sCelebrity Street StyleThe 2000s