Decades before street style was parlayed into a showcase of fashion ambassadorships or could make you a bona fide ‘It’ girl, Princess Diana inadvertently pioneered the art of off-duty dressing as the new frontier of style.

By the time she had exchanged “I dos” with King Charles III in 1981 (and cemented herself as the people’s princess in her meringue wedding dress on the balcony of Buckingham Palace), the former Princess of Wales had already established herself as a multifaceted sartorialist. One who could court the press in a strapless taffeta gown (which broke royal fashion protocol) at her first official engagement as a member of ‘The Firm’ all the while conveying her sentiment as an outsider in a ‘black sheep’ sweater at a Windsor polo match. (Editor’s Note: The sweater eventually sold for an eye-watering sum at auction decades later, if that’s any indication of her enduring appeal.)

Throughout her life in the spotlight—one that tragically ended too soon with a car accident in Paris on August 31, 1997—Princess Diana recognised the lucrative medium that was clothing, communicating her desires and darkest secrets in a perfectly constructed ensemble. (Need we direct you to her iconic “revenge dress” as proof?)

Yes, at a time when royal style rules were most stringent, the late Princess operated with a sense of chic insouciance and laissez-faire flair. This allowed for freedom—both from the strict confines placed on her as the wife of the heir to the British throne and in experimenting with her silhouette.

Rebellious, of course, in tucking tracksuit pants into cowboy boots and layering them with a pinstripe blazer and baseball hat. Even more so in the skin-baring bike shorts and varsity crew necks she wore while running to the gym, car keys clasped between her teeth. But enviable nonetheless, going on to become one of the iconic outfits of the 20th Century.

On the other end of the spectrum, her regal two-piece suits and glamorous tailored staples have proven to be a continued hit, especially with the return of 90s minimalism courtesy of the office siren aesthetic. As it goes, irrespective of what personal style formula or trend you adhere to, cues can always (and should always) be taken from Princess Diana’s street style.

In honour of what would be her 63rd birthday on July 1, we look back at her best street-style looks from her pre-royal days in the early 1980s to her post-separation finesse up until her passing. 

Princess Diana’s Best Street Style Moments