Diana, Princess of Wales

Cycling shorts and a sweatshirt, mid-1990s Leaving the Chelsea Harbour Club gym in London in coral cycling shorts, a baggy pale blue sweatshirt, white socks and chunky white sneakers. Photographers regularly waited for her outside the club after her separation, and these unplanned pictures made her one of the first famous faces of what is now called athleisure. The shorts-and-sweatshirt pairing is still one of her most copied looks.