Princess Diana's Most Iconic Style Moments

Princess Diana - Style Icon - Kate and William Wedding
Photo: Tim Graham/Corbis

Princess Diana holds a special place in the hearts of people around the world, and her iconic style continues to captivate audiences to this day. She's graced the cover of People 57 times—more than anyone in the history of the magazine. And though royal comparisons can be made (see: Princess Diana and Kate Middleton's top twinning moments), the Princess of Wales had a fashion sense all her own.

Although 20 years have passed since Diana's tragic death, her signature sartorial flair remains a classic.

Celebrate the late royal's life by revisiting her most iconic style moments, below.

01 of 26

1980

Princess Diana - Style Icon - Kate and William Wedding
Getty Images

Still lacking a royal clothing allowance, the teenaged teacher's assistant topped her romantic pink evening gown with a plain wool coat for Princess Margaret's 50th birthday bash.

02 of 26

1981

Princess Diana - Style Icon - Kate and William Wedding
Landov

She collaborated on her wedding gown with little-known design team David and Elizabeth Emanuel. "In the end, the design process was quite simple because it was just the three of us," the duo wrote in A Dress for Diana. They had the future princess slip sample dresses on over her jeans: "She was terribly excited to be trying on huge bouffant petticoats, satin skirts, and boned bodices." The final garment was made of British-woven silk and featured a dramatic 25-foot train.

03 of 26

1981

Princess Diana - Style Icon - Kate and William Wedding
Central Press/Getty

When Shy Di met with the press on her Scottish honeymoon, her finery was limited to her Welsh gold wedding ring inscribed with a message from the prince: "I Love You, Diana."

04 of 26

1982

Princess Diana - Bruce Oldfield - Style Icon - Kate and William Wedding
Jayne Fincher/Getty

The expectant princess made headlines in a single-shoulder, drop-waist Bruce Oldfield gown in vivid, blue silk. "The English rose syndrome was never my bag," the designer once told a biographer. "I liked to see her in much simpler things."

05 of 26

1985

Princess Diana - Bruce Oldfield - Style Icon - Kate and William Wedding
Jayne Fincher/Getty

The princess was nicknamed "Dynasty Di" by the tabloids because of her wide-shouldered gowns like this silver Bruce Oldfield. "She was very involved," Oldfield has said of his client's wardrobe, but, "you'd have to be fast because she didn't have much patience."

06 of 26

1985

Princess Diana - Catherine Walker - Style Icon - Kate and William Wedding
Tim Graham/Getty

Diana wore this wine, velvet Catherine Walker dress to a London premiere. Although it looked conservative from the front, the gown had an open back that the princess accentuated with a long pearl necklace worn backwards.

07 of 26

1985

Princess Diana - Victor Edelstein - Style Icon - Kate and William Wedding
Tim Graham/Getty

Designer Victor Edelstein has said that the dresses he made for the princess were a collaboration: "You each make suggestions and ask, 'What do you think?'" In the case of this white gown and bolero, the partnership paid off. Years after she wore it to a New York event, she chose a photo of herself in the ensemble for the cover of her Christie's auction catalog.

08 of 26

1985

Princess Diana - Style Icon - Kate and William Wedding
Tim Graham/Getty

For an appearance in Melbourne, Australia, Diana accented a single-shoulder gown with an emerald-and-diamond choker worn as a tiara. The necklace was a wedding gift from the queen, who likely imagined the deco treasure being worn in a more conventional way.

09 of 26

1987

Princess Diana - Style Icon - Kate and William Wedding
Tim Graham/Getty Images

Victor Edelstein based this navy, velvet column gown on Edwardian evening designs. The princess famously wore it for a spin on the White House dance floor with John Travolta.

10 of 26

1988

Princess Diana - Style Icon - Kate and William Wedding
Tim Graham/Getty Images

Proving that she needed little more than her statuesque frame to make an impression, Diana strolled the grounds at the Guards Polo Club in jeans and a sweatshirt, topped by a crisp blazer.

11 of 26

1989

Princess Diana - Style Icon - Kate and William Wedding
Tim Graham/Getty

Diana attended a U.K. wedding in a white sheath dress and dove-gray coat accessorized with a traditional British wedding hat—and an even more traditional British umbrella!

12 of 26

1989

Princess Diana - Style Icon - Kate and William Wedding
Alpha/Globe

The princess coupled her beaded ball gown from Catherine Walker with the Spencer tiara. She was known to have dresses altered for future wearings; a version of this gown with a narrow skirt would later sell at auction for $51,750.

13 of 26

1989

Princess Diana - Style Icon - Kate and William Wedding
Tim Graham/Getty Images

The high collar on this Catherine Walker pearl-encrusted bolero was inspired by Elizabethan ruffs. The less historically minded press christened the ensemble "the Elvis dress."

14 of 26

1991

Princess Diana - Catherine Walker - Style Icon - Kate and William Wedding
Glenn Harvey/Camera Press/Retna

For the Canadian premiere of Crocodile Dundee II, she chose a floral-print, ruched dress by Catherine Walker.

15 of 26

1991

Princess Diana - Style Icon - Kate and William Wedding
Tim Graham/Getty Images

Princess Diana looked radiant at a London Kire Te Kanawa concert in a raspberry-hued Victor Edelstein gown.

16 of 26

1992

Princess Diana - Style Icon - Kate and William Wedding
Tim Graham/Corbis

The princess visited the British School of Seoul in South Korea wearing a fitted green suit with matching pumps.

17 of 26

1993

Princess Diana - Style Icon - Kate and William Wedding
Tim Graham/Getty

A hot-pink frock coat and matching skirt gave the newly-separated Diana a cheerful glow.

18 of 26

1995

Princess Diana - Christian Lacroix - Style Icon - Kate and William Wedding
Jayne Fincher/Getty

As a royal, Diana was required to wear British designers to boost the local economy. Post-separation, Diana often donned international couture like this crimson Christian Lacroix dress, worn in Paris.

19 of 26

1994

Princess Diana
Rex USA

It was the LBD worth a thousand words: In 1994, just as a documentary regarding her husband's infidelities was airing, a lithe and leggy Princess Diana strolled into a Serpentine Gallery benefit wearing a figure-hugging ruched mini dress from Greek designer Christina Stambolian. The next day, every front page was devoted not to the Prince of Wales's televised confession but to images of the glowing, confident 32-year-old Diana. Ever mindful of the power of fashion, three years later she auctioned off 79 of her favorite gowns at a Christie's auction that raised $6 million for AIDS and breast cancer charities. Click on for more of the late royal's most unforgettable looks.

20 of 26

1995

Princess Diana - Versace - Style Icon - Kate and William Wedding
Tim Graham/Getty

What happened to Shy Di? The princess began to favor sheath dresses that showed off her slim shape, like this white Versace number she wore to a charity concert in Italy.

21 of 26

1995

Princess Diana - Style Icon - Kate and William Wedding
Rex USA

Diana showed off her toned shoulders in a plunging, beaded cocktail dress by Catherine Walker.

22 of 26

1995

Princess Diana - Gianni Versace - Style Icon - Kate and William Wedding
Tim Graham/Getty

Gianni Versace designed her Jackie O-inspired pink suit for a visit to the nation's troops. Her pillbox hat was from Philip Somerville.

23 of 26

1996

Princess Diana - Style Icon - Kate and William Wedding
Uppa-Ipol/Globe

Diana wore an ivory, pearl-studded shalwar kameez to a cancer fundraiser in London. The pantsuit, which was a gift from friend Jemima Khan, inspired her to commission similar Pakistani-inspired outfits from Catherine Walker.

24 of 26

1997

Princess Diana - Style Icon - Kate and William Wedding
Tim Graham/Getty Images

Diana visited patients at an Angola hospital wearing a sleeveless chambray shirt and trim chinos.

25 of 26

1997

Princess Diana - Style Icon - Kate and William Wedding
Sutcliffe/Sipa

Diana met with Mother Theresa in New York in a simple white suit and cap-toed pumps.

26 of 26

1997

Princess Diana - Style Icon - Kate and William Wedding
Tim Graham/Corbis

Her figure-hugging Catherine Walker dress and Jimmy Choo shoes accented her long legs.

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