18 Of Princess Diana’s Most Iconic Fashion And Beauty Moments

The People's Princess was a sartorial icon way ahead of her time. Ahead of The Crown's new season release, we look at some of her finest looks

As the world so tragically learnt in 1997, Princess Diana lost her life in a car accident, leaving her two young boys, Prince William and Prince Harry without their mother. Her impact though, has been far reaching in more ways than one. She refuted many royal traditions, thus paving a (slightly) more modern path for the monarchy, dedicated much of her life to humanitarian work and of course, left a strong sartorial impression that still reverberates through the industry.

From her revenge dress to the inception of collegiate-inspired athleisure, her voluminous wedding gown to her pick of the crown jewels, here we look at 18 of Diana’s most iconic fashion and beauty moments through history.

Keep scrolling for the gallery.

LONDON – NOVEMBER 1995: Princess Diana, Princess of Wales, wearing Virgin Atlantic sweatshirt, leaves Chelsea Harbour Club, London in November, 1995. (Photo by Anwar Hussein/WireImage)

Who could forget this iconic photo of Princess Diana running around town in a baggy “Fly Atlantic” pullover sweater, peach bike shorts, and chunky runners? Taffeta and ball gowns aside, Diana’s preference for athleisure is still paying fashion dividends today. Modern reincarnates like Hailey Bieber and Bella Hadid are often seen in similar ensembles, whereas lifestyle brands (like the now-questionable Sporty&Rich) reference her bike-short-preppy-logo-sweater aesthetic season after season.

TETBURY, UNITED KINGDOM – JULY 18: Princess Diana Resting Her Head In Her Hands Whilst Sitting On The Steps Of Her Home At Highgrove, Gloucestershire. (Photo by Tim Graham Photo Library via Getty Images)

BONN, GERMANY – NOVEMBER 02: The Prince And Princess Of Wales In Germany Attending An Evening Function. She Is Wearing A Dress Designed By Fashion Designer Victor Edelstein (Photo by Tim Graham Photo Library via Getty Images)

Princess Diana (1961 – 1997) arriving at the Serpentine Gallery, London, in a gown by Christina Stambolian, June 1994. (Photo by Jayne Fincher/Getty Images)

Ah, the original revenge dress. On the same day Prince Charles publicly confessed his affair with Camilla Parker-Bowles in a television interview with Jonathan Dimbleby, the Princess attended the Serpentine Gallery’s summer party wearing a custom black velvet off-shoulder dress by Greek designer Christina Stambolian. At the time it was considered the ultimate sartorial middle finger to her cheating ex-husband. And rightly so – she looks fantastic.

NEW ZEALAND – 20th APRIL 1983: Princess Diana, Princess of Wales, looks thoughtful while wearing a tiara in New Zealand during April 1983. (Photo by Anwar Hussein/WireImage)

Gifted to Diana as a wedding present in 1981, the ‘Lover’s Knot’ tiara is encrusted with diamonds and teardrop pearls. It was designed by Queen Elizabeth’s grandmother in 1914 and was reportedly Diana’s favourite.

Diana, Princess of Wales on holiday in Majorca, Spain on August 10, 1987. (Photo by Georges De Keerle/Getty Images)

Princess Diana wearing an unusual combination of white trousers, 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)

UNITED KINGDOM – MAY 02: Prince William with his mother Diana, Princess of Wales at Guards Polo Club, The Princess is casually dressed in a sweatshirt with the British Lung Foundation logo on the front of her t-shirt (Photo by Tim Graham Photo Library via Getty Images)

Diana, Princess Of Wales Attends The Victor Chang Research Institute Dinner Dance During Her Visit To Sydney, Australia. (Photo by Julian Parker/UK Press via Getty Images)

In striking blue Versace (one of her favourite designers) while on tour in Australia.

LONDON, UNITED KINGDOM – NOVEMBER 04: Princess Diana At The Victoria And Albert Museum For The Splendours Of The Gonzagas Exhibition Gala Wearing A Pale Blue Chiffon Evening Dress Designed By Fashion Designers Bellville Sassoon. The Princess Seemed Tired During The Event And The Following Day The Palace Announced Her Pregnancy. (Photo by Tim Graham Photo Library via Getty Images)

Princess of Wales by day, nap queen by night. This iconic photo of Diana at the Victoria’ and Albert Museum Exhibition Gala in pale blue Bellville Sassoon chiffon is one of her best (because all those royal engagements no doubt got exhausting).

FRANCE – UNDATED: Princess Diana, Princess of Wales poses in a bikini whilst on holiday in the South of France. (Photo by Anwar Hussein/WireImage)

London, England October 15,1994. Princess Diana shopping in Knightsbridge. (Photo by Tom Wargacki/WireImage)

MODENA, ITALY – SEPTEMBER 12: Princess Diana Attending A Concert In Italy In Aid Of Bosnian Children. The Princess Is Wearing A Short White Dress And White Shoes. (Photo by Tim Graham Photo Library via Getty Images)

BALMORAL, UNITED KINGDOM – MAY 06: Prince Charles With His Fiance Lady Diana Spencer During A Photocall Before Their Wedding While Staying At Craigowan Lodge On The Balmoral Estate (exact Day Date Not Certain) (Photo by Tim Graham Photo Library via Getty Images)

LONDON, UNITED KINGDOM – NOVEMBER 20: Diana, Princess Of Wales, Attending A Gala Evening In Aid Of Cancer Research At Bridgewater House In London. The Princess Is Wearing A Dress Designed By Fashion Designer Jacques Azagury (Photo by Tim Graham Photo Library via Getty Images)

Lady Diana famously worked closely with makeup artist Mary Greenwell (who actually trained Charlotte Tilbury). It was reportedly Greenwell who convinced Diana to steer clear of the heavy blue eyeliner she was so fond of in the 80s.

The Prince and Princess of Wales on the balcony of Buckingham Palace on their wedding day, 29th July 1981. She wears a wedding dress by David and Elizabeth Emmanuel and the Spencer family tiara. (Photo by Terry Fincher/Princess Diana Archive/Getty Images)

Princess Diana wed Prince Charles at St. Paul’s Cathedral in London. The dress, designed by David and Elizabeth Emanuel for Alexander McQueen, was covered in 10,000 pearls and featured a 25-foot train – the longest in royal history. Referred to as called “the wedding of the century,” the glamorous affair was attended by 3,500 guests and watched on television by 750 million people.