Popsugar Fashion Celebrity Fashion 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 23 September 2020 by Sarah Wasilak View On One Page Photo 16 of 23 ADVERTISEMENT () Start Slideshow Share This Link Copy ← Use Arrow Keys → 16 Nothing Is More Classic Than Jeans, Black Boots, and Fall Sweaters Previous Next Start Slideshow Celebrity FashionThe 2000sThe '90sNostalgiaCelebrity Street StyleCelebrity CouplesFall FashionJennifer AnistonRed CarpetBrad Pitt