By Ava Gilchrist

Princess Diana’s Street Style Is Definitive Proof She’s A Pioneering Trendsetter

Queen of our hearts, and of the most popular styles from the last century.
Princess Diana on holiday in Majorca, Spain on August 10, 1987. (Photo by Georges De Keerle/Getty Images)

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

Lady Diana Spencer leaves the Ritz Hotel in London after attending Princess Margaret’s 50th birthday party in November 1980. Princess Diana had only recently come to public attention as rumours of her romance with Prince Charles began to circulate. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
Lady Diana Spencer, then engaged to Prince Charles, leaving her flat at Coleherne Court in Earl’s Court, London, 12th November 1980. (Photo by Hulton Archive/Getty Images)
Princess Diana wearing the ‘black sheep’ wool jumper to Windsor Polo, June 1981. (Photo by Tim Graham Photo Library via Getty Images)
BALMORAL, UNITED KINGDOM – MAY 06: Princess Diana and Prince Charles At Craigowan Lodge, Balmoral Estate in 1981 ahead of their wedding. (Photo by Tim Graham Photo Library via Getty Images)
Princess Diana, wearing yellow dungarees with a floral blouse and red wedges, and Sarah Ferguson attend a polo match at Cowdray Park Polo Club in Gloucestershire, 12th July 1981. (Photo by Anwar Hussein/Getty Images)
LONDON, UNITED KINGDOM – DECEMBER 08: At the Royal Marsden Cancer Hospital in 1992. (Photo by Tim Graham Photo Library via Getty Images)
During a visit to Swindon, UK, February 1985, wearing a red tartan suit by Caroline Charles. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
Wearing a navy blue sweater and straight-leg white pinstripe trousers at a Guards Polo Club match at Smiths Lawn, Windsor, May 1986. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
Princess Diana and Prince William attend the St Mary Abbots Church Christmas concert in Kensington, London, 15th December 1987. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
WINDSOR, UNITED KINGDOM – MAY 02: At the Guards Polo Club. Her combination of cowboy boots, a blazer and baseball cap has since become one of her most iconic silhouettes. (Photo by Tim Graham Photo Library via Getty Images)
Princess Diana wearing white track pants, cowboy boots, a blazer jacket and a baseball cap after taking her sons to school at Wetherby, 25th April 1989. (Photo by Daily Mirror/Mirrorpix/Getty Images)
LONDON, UNITED KINGDOM – MAY 25: Visiting Sarah, Duchess of York, and the newborn Princess Eugenie at The Portland Hospital March 5, 1990 in London, England. (Photo by Georges De Keerle/Getty Images)
Attending the christening of Princess Eugenie at St Mary Magdalene Church in Sandringham, UK, 23rd December 1990. She is wearing a red, black and white houndstooth patterned suit by Moschino. (Photo by Princess Diana Archive/Getty Images)
Wearing a Philadelphia Eagles jacket to drop off her son Prince Harry at Wetherby School in London, January 1991. Prince William is leaving with her. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
With Prince William outside St George’s Chapel, Windsor, at Easter, April 1992. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
Visiting St George’s Hospital in London, 15th September 1993. (Photo by Jayne Fincher/Princess Diana Archive/Getty Images)
AUSTRIA – MARCH 26: Running whilst on a skiing holiday in Lech, Austria (Photo by Tim Graham Photo Library via Getty Images)
LONDON, ENGLAND — OCTOBER 15, 1994:. Shopping in Knightsbridge. (Photo by Tom Wargacki/WireImage)
LIVERPOOL, UNITED KINGDOM – NOVEMBER 07: Visiting Liverpool wearing an orange suit by Versace and carrying a Dior bag. (Photo by Tim Graham Photo Library via Getty Images)
MODENA, ITALY – SEPTEMBER 12: Attending a Concert In Italy. (Photo by Tim Graham Photo Library via Getty Images)
CANTERBURY, ENGLAND – MAY 20: Wearing a pink suit by Versace and a pillbox hat by Philip Sommerville to inspect members of the Queen’s and Royal Hampshire Regiment, during a visit to Howe Barracks on May 20, 1995 in Canterbury, United Kingdom. (Photo by Anwar Hussein/Getty Images)
BUENOS AIRES, ARGENTINA – NOVEMBER 23: At Buenos Aires Airport for her historic visit to Argentina. The Princess wore a Versace suit and carried a Christian Dior bag. (Photo by Tim Graham Photo Library via Getty Images)
LONDON, UNITED KINGDOM – DECEMBER 02: At Centrepoint’s Christmas campaign at Piccadilly, London. (Photo by Tim Graham Photo Library via Getty Images)
LONDON – NOVEMBER 1995: Wearing a Virgin Atlantic sweatshirt, leaves Chelsea Harbour Club, London in November 1995. (Photo by Anwar Hussein/WireImage)
Having lunch with her step-mother, Raine Spence, at The Connaught Hotel in Mayfair. (Photo by Antony Jones/UK Press via Getty Images)
LONDON, UNITED KINGDOM – MARCH 10: Leaving St. George’s Church in Hanover Square, London, after attending the Memorial Service for photographer Terence Donovan. (Photo by Tim Graham Photo Library via Getty Images)

This story first appeared on GRAZIA International.