Princess Diana’s 22 Most Controversial Outfits

Her Philadelphia Eagles jacket

Given to her by statistician Jack Edelstein, a close friend of Grace Kelly, a “man about town” who “befriended politicians and millionaires and hung out with comedians Don Rickles and Jerry Lewis”, Diana’s Philadelphia Eagles jacket caught attention because it was, 1) very casual, and 2) very American. Newspapers splashed the image across front pages, claiming Diana’s sporty look was a “struggle to find herself” after her divorce.