Princess Diana's Most Inappropriate Outfits
Christopher Snyder
Updated on October 08, 2026
If we could model our closets after Princess Diana, we would — her iconic collection of sweatshirts, ranging from her Harvard design to her Atlantic pullover, continue to inspire the best casual outfits out there. But Diana really challenged the rules when she wore a sweatshirt with U.S.A. and the American flag printed on the front.
As noted by Cosmopolitan, the royals do not often show a love of country quite like Diana did, even when traveling diplomatically. It's common for a member of the royal family to pay subtle homage to other countries (like when Kate Middleton wore a maple-leaf hat on Canada Day), but to go as far as wearing a sweatshirt that most of us would choose for the Fourth of July is a whole different ball game.
Despite the clear defiance that Diana was displaying with her casual look, people still adored her style and, as such, were eager to pay top dollar for pieces of her wardrobe. A similar U.S.A. sweatshirt in Diana's closet was expected to sell for over $10,000, as noted by People. We'll stick to Gap for our U.S.A. looks.