“Every single session all the media were outside camped with their stepladders, and cameras and lenses and everything,” her personal trainer Jenni Rivett recalled in a 2018 interview. “ It wasn’t her that asked for all this. I remember one of her strategies was that she was going to wear the same Virgin Active sweatshirt every single session.”
A side effect of her dedication to sartorial repetition is that the style became synonymous with Diana herself. Plus, whereas much of what Princess Diana wore was custom or designer, this outfit was decidedly—and achievably—high street. “It’s not the combination itself that is novel—that’s what people worked out in at the time,” says Vogue’s senior runway editor Laia Garcia-Furtado. “But on her, it becomes transformed, perhaps because it was so rare to see someone of her stature ‘dressed down’—and also because it is endowed by her ineffable allure.”
Princess Diana leaving Chelsea Harbour Club in 1994.Photo: Getty Images
During the 2010s, internet and social media culture reached its full power. Pictures of Diana weren’t just in magazines or newspapers, but all over blogs, Twitter feeds, and Instagram Discover pages. It was also around this time that athleisure became a major trend, with companies like Lululemon and Alo Yoga hitting billion-dollar revenues. Suddenly, Diana’s ’90s gym clothes felt downright fashionable. And in 2019, it all hit a fever pitch when Hailey Bieber—an extremely influential fashion figure in her own right—recreated Diana’s bike shorts and sweatshirt look for a Vogue France editorial. The images went viral.