See Princess Diana's Fashion Evolution in 40 Pictures

  • Diana selected a deep blue skirt suit and white pussy bow blouse for her official engagement photos in 1981; the suit's color complemented the sapphire engagement ring she received from Prince Charles.
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  • Ahead of her wedding, Diana went casual with a cozy sweater and a pair of classic Wellie boots while at the British royal family's holiday home, Balmoral Castle, in Scotland.
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  • Diana's maximalist wedding gown for her July 29, 1981 wedding to Prince Charles was a joint collaboration between the princess and husband and wife design duo David and Elizabeth Emanuel. The dress had a 25 foot train and was made in just 3 months.
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  • The princess wore a casual but chic Bill Pashley suit at Balmoral during her honeymoon.
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  • For the Braemar Games in September 1981, Diana sported a tartan outfit by Caroline Charles.
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  • At an exhibit opening at the Victoria And Albert Museum, Diana wore a Bellville Sassoon gown; she famously fell asleep while sitting up at this event, adding to public speculation that the princess was expecting. It was later revealed that she was pregnant with Prince William at the time.
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  • After giving birth to Prince William on June 22, 1982, Diana exited the hospital wearing a playful polka dotted shift dress.
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  • Diana's bright blue, drop-waist Bruce Oldfield dress worn to a fashion show in November 1982 caused plenty of buzz because it showed off how slender the princess had become, less than a year after giving birth to Prince William. She later revealed that she had suffered from eating disorders during the early days of her marriage to Prince Charles.
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  • Call it sartorial diplomacy, but Diana usually sported red and white ensembles during royal trips to Canada; here, she wore a coordinating hat and red and white polka dot suit in June 1983.
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  • Princess Di had a menswear moment during a trip to Italy in April 1985.
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  • To visit the Pope at the Vatican, Diana modestly covered her head with a veil.
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  • As Diana became more comfortable with her role as the princess, she took more style risks, like this angular, shoulder pad-adorned blue Bruce Oldfield dress with a nipped-in waist that she wore in Venice in May 1985.
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  • Princess Di's sleek red Bruce Oldfield gown that she donned for a trip to Australia was a far cry from the floral and frilly dresses she had worn in her early days as a princess.
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  • Princess Diana didn't shy away from bold fashion choices, often selecting dresses in vibrant colors. Here, her teal gown was nicely complemented by her repurposing a choker from the royal family as a tiara of sorts.
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  • Diana's backless and metallic Bruce Oldfield dress in November 1985 earned her the nickname "Dynasty Di" because of the parallels between the look and the flashy TV show.
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  • This black velvet, off-the-shoulder Victor Edelstein dress that Diana first sported at the White House in 1985 became known as the "John Travolta" dress because Diana shared a dance with him in it.
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  • For the wedding of Prince Andrew and Sarah Ferguson, Princess Di wore a turquoise polka dotted suit and matching hat.
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  • For a state dinner in Saudi Arabia in 1986, Diana wore a dramatic gown designed by the duo behind her famous wedding dress, the Emanuels.
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  • While at the Guards Polo Club in 1988, the princess proved that she could do off-duty style as well as formal wear when she paired jeans and a sweatshirt with an oversized blazer. A baseball cap was the perfect insouciant accessory.
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  • While in Dubai in 1989, Diana wore a Catherine Walker suit and matching Philip Somerville turban hat; the hat was as stylish as it was modest, showing her respect for the customs of the land.
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  • Diana's Catherine Walker suit and matching Philip Somerville hat took color blocking to the next level during a visit to Kuwait.
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  • Di's chose a sleek silhouette with this two-toned gown while attending the ballet in 1989.
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  • This embellished white gown that Diana wore in Hong Kong in 1989 was dubbed the "Elvis dress" by the press. The princess paired the Catherine Walker look with her favorite Cambridge lover's knot tiara.
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  • All eyes were on Diana when she showed up to a state dinner in Budapest in 1990 wearing a stunning and slim white column dress by Catherine Walker with a pearl choker.
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  • The princess put on the glitz when she sported a blue glitter Catherine Walker dress to attend the Diamond Ball in 1990.
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  • Diana modestly covered her head during a visit to the Badshahi Mosque in Pakistan in 1991.
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  • The Princess wore colorful suit separates for a highly-photographed 1992 trip to the Taj Mahal that many point to as the height of the tension in her marriage to Prince Charles.
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  • For the wedding of Lady Helen Windsor to Tim Taylor in 1992, Diana wore a bright green suit and a matching hat.
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  • Call it the dress seen 'round the world — amid reports of Prince Charles' infidelity in June 1994, Diana sported a body-conscious little black dress by Christina Stambolian.
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  • To honor her favorite designer Catherine Walker at a fashion awards ceremony in NYC, Diana wore a sleek navy gown of Walker's design.
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  • Diana channeled Jackie O in 1995 with a pink Versace suit and matching Philip Somerville hat.
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  • Following her separation from Prince Charles in 1992, Diana's wardrobe appeared to experience its own kind of freedom — here at a Vanity Fair party in 1995, the princess sports a short, glittery halter dress.
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  • While the princess was a strong supporter of British fashion, she also loved glamorous international design houses; here, at a 1995 concert in Italy, she wears a white dress from Versace.
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  • For a dinner in her honor in 1995 in Paris, Diana selected a dress by Christian Lacroix.
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  • Even though Diana was mostly spotted in glamorous get-ups, she could rock casual looks too — here, in November of 1995, a month before her official divorce from Prince Charles, she wears a sporty pair of shorts and a Virgin Atlantic sweatshirt.
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  • The princess paired a purple gown by Versace with a matching Jimmy Choo bag for an event in 1996.
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  • Diana wore a shalwar kameez, a gift from friend Jemima Khan, to a 1996 benefit given by Khan's husband, cricketer Imran.
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  • For a trip to Angola doing aid work in 1997, Diana dressed practically in a sleeveless chambray button-down and a pair of khaki pants.
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  • The princess wore a simple white suit and low heels to meet with Mother Teresa during a trip to New York in 1997.
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  • While vacationing in the South of France in 1997, Princess Diana sported a floral bikini; she later died in a car crash on that same trip.
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By Cady Lang

Princess Diana’s status as a style icon has become just as much a part of her legacy as the “People’s Princess” as her humanitarian work and her love for children. However, the princess’ celebrated sense of style holds up as more than just a fashion statement — it’s a visible testament to her evolution as a person. While Diana’s taste in fashion was always elegant, her selections as newly-wed 20-year-old differed drastically from the glamorous ensembles she would later sport after she had grown in both years, confidence, and wisdom.

From the demure deep blue suit she wore for her official engagement photos to the gorgeous black velvet gown and tiara she wore to dance with John Travolta at the White House, here’s a look back at Diana’s fashion evolution.

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Write to Cady Lang at cady.lang@timemagazine.com.

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