36. Jay-Z with the wifebeater in "Big Pimpin."
Hip-hop has a storied history with what are supposed to be undergarments. Artists are notorious for exposed boxers above sagging pants, and, wifebeaters-formally known as A-shirts. Hov wasn't the first to wear one in public, but he was the first to wear one in a rap video, on a yacht, with models, and Cristal. Suddenly casual was the new luxe.