Princess Diana's style has been endlessly dissected over the years, but some of her most memorable outfits were surprisingly casual—and very Americanized. Take the oversized collegiate sweatshirts she wore with her famous bike shorts to her London gym. Paired with chunky sneakers and luxury handbags, these American-inspired pieces were a regular part of her wardrobe—and she also wore more on-the-nose "USA" and American flag styles. The late princess held a genuine appreciation for American culture, and that even extended to where she shopped.
In Dianaworld: An Obsession, author Edward White explores Diana's fascination with the United States, writing how the late royal had "long looked upon America as a place of immense glamour and excitement." And as her marriage began to fail, she "continued to regard the United States as a fabled place of promise."
In terms of her wardrobe, the princess began experimenting with her wardrobe after her 1992 separation from Prince Charles, wearing shorter hemlines and more casual looks (see: her legendary Revenge Dress). But her style also became more Americanized, as White notes in Dianaworld. "One of the reasons Diana is perceived to have launched a sartorial rebellion against the House of Windsor is her wardrobe of clothing that marked her out as an Americanophile: cowboy boots, NFL sweatshirts, baseball caps, T-shirts and jackets with the stars and stripes on them."
Princess Diana owned numerous Americana-themed sweatshirts.
Diana is pictured at a JCPenney store in Virginia during a 1985 visit to the United States.
The late royal, seen with Prince William and Prince Harry, often wore a Philadelphia Eagles varsity jacket.
White continues that Diana "embraced the same philosophy of consumption that made America great—to the extent that when she was in the United States, Diana shopped at JCPenney."
While it might seem unbelievable to spot the People's Princess browsing through a rack of Liz Claiborne looks, her love of the '80s mall staple might have started during an official visit to one of its stores in November 1985. While visiting the United States with Prince Charles, Diana toured a Springfield, Virginia JCPenney and was photographed with her husband while taking in the store's selection of clothing and jewelry.
It's often been reported that Princess Diana pondered a move to America in the last few years of her life; per White, the royal "was reportedly considering whether to purchase Julie Andrews's house in the Hollywood Hills" shortly before her tragic 1997 death.
Whether or not she would have ever packed up and headed west, we'll never know, but Prince Harry and Meghan would later go on to fulfill Diana's American dream by moving to Montecito, California. Although he's likely not a JCPenney shopper, Harry has shared how much he loves Southern California life. Speaking about his new chapter during the 2024 New York Times Dealbook Summit, the Duke of Sussex said it was "the life my mum wanted for me."
