When flipping through the coolest photos of Princess Diana, there’s always one thing that runs through my mind — imagine if a royal were to wear bike shorts today? The scandal! Even more than her inimitable fashion sense was her rebellious spirit, which is why I am more than okay with Diana’s ’90s style shaping our wardrobes once again.
Around the time of Diana’s divorce from Prince Charles between 1991 and 1996, the Princess of Wales began wearing very short and slinky dresses to public engagements. When off-duty, she would wear surprisingly casual — and American — pieces like cowboy boots, baseball caps, and bike shorts. The “revenge dress” was perhaps the princess’s most iconic fashion moment, when she turned up to a 1994 Serpentine summer party in a form-fitting Christina Stambolian black silk dress, and looked incredible on the same night that Charles subtly confessed to cheating with Camilla.
The Christina Stambolian dress may be the most memorable of Diana’s evening wear, but the princess was most often seen in scoop-neck minidresses designed by Gianni Versace himself. For daytime engagements, Diana loved a Dior Lady Bag paired with a pastel skirt suit (above the knees, of course). But it wasn’t all designer names in her wardrobe; Diana was equally photographed in very casual, and sometimes athletic looks — like oversize jumpers with bike shorts and white trainers, or boots worn over trousers with a baseball cap.
Key to Princess Diana’s style is her use of bold colours and eye-catching prints. Pairing red and purple in one outfit was an unusual and inspiring choice for a trip to Hong Kong. She also contrasted different coloured check prints in one outfit in a way that looked playful and smart. One of our favourite ’90s looks by the people’s princess were her slinky, monochromatic silk-satin maxi dresses — where she would often choose one jewel-tone colour, like cobalt or violet, and wear it head-to-toe with matching shoes and a clutch.
Want more ’90s styling tips from Princess Diana? Keep reading ahead for her best looks and where to shop similar pieces.
