Princess Diana's evolution from a shy, ruddy-cheeked country bumpkin into a fashion icon happened right before our eyes. When she first appeared on the arm of Prince Charles her outfits embodied youth and innocence: Fair Isle sweaters, Laura Ashley-esque ensembles and ruffled gowns in girly fabrics like chiffon and taffeta. And her wedding dress just may be the best example of her lack of style savvy: an enormous meringue of a gown with a legendarily long train. But as Diana gained confidence, so did her wardrobe. In fact, the moment that signaled her transformation was the outfit she stepped out in the day after Charles's public announcement of his indiscretions: a sexy, off-the-shoulder black number by Christina Stambolian. From then on, gone were the modest high-collared dresses and Dallas-era power suits, replaced by figure-skimming sheaths and gowns by designers like Valentino, Versace, Ungaro and Chanel.
Signature items: the LBD, chinos, white button-downs, anything red, slim sheath dresses, tailored pants and dress suits.