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Princess Diana’s Best Style Moments: Her Most Iconic Fashion Photos

Diana, Princess of Wales. Tim Graham Photo Library via Get

Where protocol and image were prioritized within the British royal family, Princess Diana focused on creating a genuine connection with people from the start. Whether serving as a patron to artistic organizations like the English National Ballet, helping to end the stigma around HIV/AIDS by removing her gloves to shake hands with a patient, or participating in a barefoot race with other parents at her son’s school, Diana brought a refreshing approachability to the royal family. It was this break from rigidity and formality, in fact, that helped to cement the Princess of Wales as the “people’s princess.” 

In many ways, that authenticity was reflected in Princess Diana’s wardrobe, too. Just 20 years old when she married Prince Charles (now King Charles III) in a televised ceremony viewed by more than 750 million people around the world, Diana’s earliest looks mirrored the frills and the ruffles of the early ‘80s. But even then, there were glimmers of her personality in her royal wardrobe. The Princess of Wales would often repeat gowns from royal engagements to red carpet events (and vice versa), and she found inventive ways to accessorize with her jewelry—from wearing an emerald necklace as a headband to redesigning a sapphire brooch into her most memorable pearl choker.

She also took into consideration the cultures of the countries she was visiting during official royal tours to places like Japan and Pakistan. “My wife and I spent a great deal of time researching what she wore for official visits abroad, even visiting countries in advance to make sure we had it right,”recalled Said Cyrus, the husband of Diana’s go-to designer Catherine Walker. “We tried to ensure that our designs bridged her ambassadorial role for her own country and also paid respect to each destination.”

Following her separation from Prince Charles in 1992 (the pair finalized their divorce in 1996), Princess Diana’s style shifted to reflect her newfound independence. Bright colors were still a part of her wardrobe, but she also added more neutrals, most often turning to Gianni Versace for tailored suits and sleek evening gowns. Her handbag of choice also became a focal point, with several fashion houses later renaming popular bags in her honor. There was the Gucci tote with bamboo top handle, that would officially be renamed the Gucci Diana when then-creative director Alessandro Michele reissued the bag in 2021, and Tod’s renamed one of its leather totes the Di bag as well. Most famous of all was the Dior Chouchou bag, which was first gifted to Diana by France’s first lady Bernadette Chirac in 1995, and became such a constant accessory for the Princess of Wales that within a year, the French fashion house changed its name to the Lady Dior.

And then, there was her off-duty style. While polo matches and school runs often meant pairing denim with blazers and flats, it’s Princess Diana’s workout wear, which combined oversized sweatshirts, bicycle shorts, crew socks and sneakers, that continues to be emulated today. Ahead, revisit some of Princess Diana’s best fashion moments—from royal tours in custom evening gowns and diamond tiaras to off-duty athleisure looks.

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Lady Diana Spencer With Prince Charles. Tim Graham Photo Library via Get

1981, Buckingham Palace

To officially announce their engagement, a 19-year-old Lady Diana Spencer wore a blue skirt suit that matched her sapphire and diamond engagement ring as she posed alongside Prince Charles in the gardens of Buckingham Palace. Before she suddenly found herself in the spotlight, she had been working as a teacher’s assistant at a nursery school in London.

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Lady Diana Spencer and her fiancé, Prince Charles. Getty Images

1981, Cowdray Park Polo Club

One of the earliest examples of Diana’s off-duty style, the princess-to-be attended a polo match just weeks before her wedding in buttercup-yellow overalls that she wore with a floral print blouse, espadrille sandals and sunglasses.

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Prince Charles and Lady Diana Spencer. Getty Images

1981, Royal Wedding

In a ceremony more extravagant than any fairytale, Lady Diana Spencer became the Princess of Wales when she wed Prince Charles at St. Paul’s Cathedral in London. For her walk down the aisle, which would make history as the first televised royal wedding, Diana wore a silk-taffeta design by David and Elizabeth Emanuel. The very ‘80s gown included oversized sleeves and a full skirt, with nearly 10,000 mother of pearl sequins hand-sewn along the bodice and sleeves (and the 40-foot-long veil). An impressive 25-foot detachable train trailed behind the princess, who also wore custom slippers by Clive Shilton, the Spencer family diamond tiara and diamond drop earrings.

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Diana Princess of Wales. Tim Graham Photo Library via Get

1981, Victoria & Albert Museum

To attend an exhibition at the Victoria & Albert Museum, Diana wore a shimmering pastel gown by Bellville Sassoon that was accented with tiny pale blue ribbons and a larger version at the waist. The off-the-shoulder silhouette also proved to be the perfect way to show off her multi-strand pearl and diamond choker necklace, which was complemented with a matching pearl bracelet and diamond drop earrings.

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Diana, Princess of Wales. Getty Images

1982, Scilly Isles

Breezy dresses in bright colors were a staple for Diana throughout her pregnancy with her first son, Prince William, with this long-sleeve design being a prime example. Princess Diana would wear a green polka-dot gown a few months later when she and Prince Charles were pictured leaving the hospital with their son, and just over 30 years later, Kate Middleton would follow suit in her own light blue polka-dot dress while leaving the very same hospital with her and Prince William’s newborn son, Prince George.

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Diana, Princess of Wales. Getty Images

1983, in Australia

Diana wore this floral print pink dress with a matching hat during her first overseas engagement—a six-week tour of Australia and New Zealand.

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Diana, Princess of Wales. Tim Graham/Getty Images

1983, in Canada

A few months later in Canada, Diana wore a blue gown with lots of frills by Bruce Oldfield, which she paired with a metallic belt and clutch. As she was attending a formal dinner, the Princess of Wales accessorized with her Spencer family tiara and the Royal Family Order pin that was given to her by Queen Elizabeth II.

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Diana, Princess of Wales with Major Ronald Ferguson. Getty Images

1983, Guards Polo Club

Princess Diana wore this wool sheep jumper by Warm & Wonderful to two polo matches: first in 1981 and then again, pictured here, in 1983. For her Guards Polo Club appearance, Diana wore the sweater, which included one black sheep among the knitted white sheep, over a white blouse with a large collar and black ribbon. The sweater has since been renamed by the company in her honor, and in 2023, Diana’s original sheep jumper sold for $1.14 million at Sotheby’s auction house in New York.

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Diana, Princess of Wales. Getty Images

1984, Visiting Odstock Hospital

Adding suits to her maternity style, Princess Diana wore this blue set by Jan Van Velden to meet with patients and staff at the Odstock Hospital in Salisbury, England, while pregnant with Prince Harry. Her look included a blue hat with mesh veil by milliner John Boyd, and Diana matched her accessories to the white square collar on the suit with white pumps and clutch bag.

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Diana, Princess of Wales. Getty Images

1985, The La Scala Opera House

Princess Diana had many memorable fashion moments during her 17-day tour of Italy with Prince Charles in 1985 (including a black-veiled ensemble during her audience with Pope John Paul II), but this pink Victor Edelstein gown was most fit for a royal. The sleeveless design, with its fitted bodice and flowy skirt, was just right for a night at the La Scala opera house, and Diana accessorized with a pearl necklace, pearl drop earrings and the Lover’s Knot tiara; a collection of diamonds and hanging pearls that was originally made for Queen Mary in 1913. This particular tiara would eventually prove to be a favorite of Kate Middleton’s

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Diana, Princess of Wales. Getty Images

1985, in Australia

For a gala event in Australia, Diana wore a custom one-shoulder satin evening gown by David and Elizabeth Emanuel. But it was her emerald and diamond headband that really stole the show; it was originally an Art Deco style choker that was given to Queen Mary by the Maharani of Patiala in 1911.

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Diana, Princess of Wales. Getty Images

1985, in Australia

During her 1985 Australian tour, Princess Diana also attended the Melbourne Cup horse race, where she donned a white and black suit by Bruce Oldfield. Milliner Frederick Fox created a matching hat, and Diana added black gloves, a clutch bag, pumps and seam tights with tiny bows at the ankle.

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Diana, Princess Of Wales, with Nancy Reagan. Tim Graham Photo Library via Get

1985, in the U.S.

During an official visit to the U.S., Princess Diana attended a dinner at the White House, where she met with President Ronald Reagan and first lady Nancy Reagan (and famously danced with John Travolta). For the formal event, Diana wore a velvet off-the-shoulder gown in midnight blue by designer Victor Edelstein, which she paired with evening gloves, sapphire and diamond earrings, and a massive sapphire and diamond necklace (the latter was originally gifted by the Queen as a brooch before Diana had it converted into a seven-strand pearl choker).

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Diana, Princess of Wales. Tim Graham Photo Library via Get

1987, Cannes Film Festival

At the Cannes Film Festival, the Princess of Wales channeled another royal—Princess Grace Kelly of Monaco—when she wore this strapless powder-blue gown by Catherine Walker. The custom silk chiffon design was said to be inspired by a similar gown that Kelly had worn on-screen in Alfred Hitchcock’s 1955 film, To Catch a Thief. Similar to Kelly’s character, Frances Stevens, Diana wore a matching scarf, but she added statement jewelry with aquamarine and diamond earrings and a bracelet.

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Diana, Princess of Wales. Tim Graham Photo Library via Get

1988, in Australia

During her next royal tour of Australia, Diana was pictured in a pink and blue patterned gown by Catherine Walker, which she wore with sapphire and diamond jewelry.

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Prince William with his mother Diana, Princess of Wales. Tim Graham Photo Library via Get

1988, Guards Polo Club

Bringing Prince William along to a polo match at the Guards Polo Club, Diana dressed casually in blue jeans and a black blazer worn over a British Lung Foundation sweatshirt. To complete the look, she added a baseball cap and cowboy-inspired brown boots.

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Diana, Princess of Wales. Tim Graham Photo Library via Get

1988, Claridge’s Hotel

Princess Diana brought back the emerald and diamond choker necklace for a banquet hosted by the president of Turkey at Claridge’s Hotel in London in 1988. The emerald jewels matched her one-shoulder gown, which was also decorated with the Royal Family Order pin and accessorized with the Spencer family tiara.

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Diana, Princess of Wales. Getty Images

1988, in France 

During her royal tour of France, Diana attended a dinner at the British Embassy in Paris wearing a red and black floral gown by Catherine Walker, which included a one-shoulder silhouette and a dramatic full skirt.

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Diana, Princess of Wales. Tim Graham Photo Library via Get

1989, Swan Lake Performance

When Russia’s Bolshoi Ballet visited London, Diana attended a performance of the company’s Swan Lake in a gown by Catherine Walker. The fitted silhouette included long sleeves and an open back, with Princess Diana coordinating her accessories to the ballet-pink skirt. While she kept her jewelry more minimal, the sleeves of the dress included pearl accents on the cuffs and Diana added pearl and diamond drop earrings.

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Diana, Princess of Wales. Tim Graham Photo Library via Get

1989, in Hong Kong

Dubbed the “Elvis Dress” by Princess Diana herself, this beaded Catherine Walker gown included a matching bolero with an estimated 28,600 hand-embroidered pearls (and, of course, the Elvis-like high collar behind its nickname). One of the dresses she would rewear, Diana originally debuted the gown at the British Fashion Awards in October before wearing it a month later during an official visit to Hong Kong. While there, Diana added even more pearls (and some diamonds) to the look with the Lover’s Knot tiara, a three-strand pearl bracelet and her pearl drop earrings.

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Diana, Princess of Wales. Getty Images

1990, in Cameroon

While visiting with deaf students at a school in Cameroon, Princess Diana wore a buttercup-yellow skirt suit by Catherine Walker, which was trimmed with a pink collar and buttons and accessorized with a pink hat by Philip Somerville.

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Diana, Princess of Wales. UK Press via Getty Images

1990, The Hunt For Red October Film Premiere

For the London premiere of The Hunt for Red October, Diana chose a shimmering emerald-green gown by Catherine Walker and matching satin pumps.

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Prince Charles and Diana, Princess of Wales. Getty Images

1990, in Hungary

When Diana attended a dinner hosted by the Hungarian president during her tour of the country in 1990, she appeared to be rewearing the “Elvis Dress” once again—this time, without the jacket. She also accessorized the look differently, with her sapphire and diamond pearl choker.

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Diana, Princes Of Wales. Tim Graham Photo Library via Get

1990, in Hungary

This pink and purple suit by Catherine Walker would prove to be a favorite of Princess Diana’s, as she would go on to wear it several times over the next two years.

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Diana, Princess of Wales. Getty Images

1990, London City Ballet Gala

As patron of the London City Ballet, Diana was on hand to chat with attendees when the company held a benefit event in Washington, D.C. For the occasion, she wore a red gown by Victor Edelstein with matching clutch and pumps, as well as her three-strand pearl bracelet and diamond and pearl earrings (both of which have been worn by Kate Middleton).

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Diana, Princess of Wales. Getty Images

1990, Princess Eugenie’s Christening

Not one to shy away from color or pattern, Diana embraced both when she attended Princess Eugenie’s christening in a red and black houndstooth pattern Moschino suit that she wore with a red hat, black gloves and two-tone pumps.

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Diana, Princess of Wales. Getty Images

1991, in London

Princess Diana incorporated NFL merch into her off-duty wardrobe when she wore a Philadelphia Eagles varsity jacket to take Prince Harry to school in 1991. The jacket was actually made for Diana as a gift from the Eagles’ then-owner Leonard Tose and the team’s statistician Jack Edelstein after she met the latter at Princess Grace Kelly’s funeral (Kelly was originally from Philadelphia).

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Diana, Princess of Wales. Getty Images

1991, in Brazil

During a visit to Brazil, Princess Diana wore a safari-inspired khaki suit by Catherine Walker that included an oversized matching belt at the waist.

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Diana, Princess of Wales. Getty Images

1991, in London

To visit the Royal Star & Garter home for injured servicemen in London, Diana opted for a simple pink and lilac-trimmed dress by Catherine Walker, which she would wear again in Pakistan, Calcutta and Egypt.

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Diana, Princess of Wales. Getty Images

1991, in Pakistan

The bright green Catherine Walker dress that Princess Diana wore in Pakistan included a coordinating headscarf for her visit to the Badshahi Mosque.

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Diana, Princess of Wales. Getty Images

1992, in India

Princess Diana wore another Catherine Walker gown to attend a banquet in India. The design included a glittering embroidered bodice, which Diana played up with the Spencer family tiara and diamond and pearl earrings.

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Diana, Princess of Wales. PA Images via Getty Images

1992, in London

Shortly before the release of her authorized biography by Andrew Morton, Diana was photographed on a school run in a casual-chic combo of black pants and a black blazer worn over a red blouse.

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Diana, Princess of Wales. UK Press via Getty Images

1993, Accidental Hero Film Premiere

In the months following her separation from Prince Charles, Diana attended the film premiere of Accidental Hero in a mint-green gown by Catherine Walker. The off-the-shoulder silhouette included white stripes and button details along the bodice, and Diana added satin pumps, a white clutch and diamond earrings to complete the look.

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Diana, Princess of Wales. Getty Images

1994, Serpentine Gallery

If there’s one dress that Princess Diana is known for, it’s this fitted, off-the-shoulder design by Christina Stambolian, which included an asymmetrical hemline and chiffon train. Paired with her favorite sapphire and diamond seven-strand pearl choker, the little black dress was soon dubbed the “Revenge Dress,” as Diana wore it to a gala event the same evening Prince Charles admitted that he had been unfaithful to her in a televised interview.

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Diana, Princess of Wales. Tim Graham Photo Library via Get

1995 in Argentina

Post-separation, Diana’s sartorial shift saw her in shorter hemlines and luxury designer pieces. This pink Versace skirt suit was an early example, which Diana wore with the square-shaped Dior Chouchou bag that would soon be renamed the Lady Dior.

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Diana, Princess of Wales. Tim Graham Photo Library via Get

1995, in Liverpool

In another Versace suit—this time, a statement-making orange—Diana attended the opening of the Liverpool Women’s Hospital. Diana wore the set with all-black accessories, though she did match her gold earrings to the hardware on her Lady Dior bag.

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Diana, Princess of Wales. Tim Graham Photo Library via Get

1996, in London

For a lunch event at Brown’s Hotel in London, Princess Diana arrived in a white coat by Versace, which she paired with pearl jewelry and her Lady Dior bag.

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Diana, Princess of Wales. Tim Graham Photo Library via Get

1996, in Chicago

During a visit to Chicago where she helped to raise nearly $1.5 million for cancer research beneficiaries, Princess Diana swapped out her Lady Dior bag for a Chanel design. Diana paired the bag, which would later be renamed the Chanel Diana by the fashion house’s then-creative director Karl Lagerfeld, with a mint-green suit and four-strand pearl choker necklace.

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Diana, Princess Of Wales. Tim Graham Photo Library via Get

1996, in Chicago

While still in Chicago, Diana attended a gala event at the Field Museum wearing a purple evening gown by Versace. The monochromatic ensemble included a clutch by Jimmy Choo, and Diana added her sapphire earrings and an eleven-strand pearl choker necklace to complete the look.

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Diana, Princess Of Wales UK Press via Getty Images

1996, in Washington, D.C.

A month after her divorce from Prince Charles was finalized, Princess Diana headed to a gala in Washington, D.C., where she teamed up with Vogue editor-in-chief Anna Wintour, The Washington Post’s then-owner Katharine Graham and fashion designer Ralph Lauren to raise money for breast cancer research. Serving as the honorary chairman of the event, Diana wore a white lace halter gown by Catherine Walker and sapphire and diamond jewelry.

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Diana, Princess Of Wales. UK Press via Getty Images

1996, in Australia

In another colorful look from Versace, Diana wore a blue one-shoulder gown while visiting Australia, which she accessorized with some of her favorite pearl pieces, as well as her new emerald-cut aquamarine ring by Asprey (a piece that Meghan Markle would later wear when she married Prince Harry).

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Diana, Princess of Wales. Patrick McMullan via Getty Image

1996, Met Gala

Given her fondness for her Lady Dior handbag, it was only fitting that Princess Diana attended the Christian Dior-themed Met Gala in New York City. To complement her favorite bag, Diana wore a navy slip dress by Dior’s then-creative director John Galliano, which was trimmed with black lace and worn with Diana’s other favorite accessories: her sapphire and diamond choker and earrings.

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Diana, Princess Of Wales. Tim Graham Photo Library via Get

1997, in Angola

Princess Diana was largely focused on her children and her charity work following her divorce from Prince Charles, and in 1997, she was introduced to the HALO Trust during her visit to Angola with the British Red Cross. The humanitarian organization, which focuses on clearing landmines, immediately earned Diana’s support. Pictured here in a casual white button-down shirt, khaki pants and matching loafers, Princess Diana’s meeting with landmine survivors and the media coverage surrounding her walk through a cleared lane in one of Angola’s active minefields were reported to have played a part in the United Nations Mine Ban Treaty that was signed shortly after her death.

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Diana, Princess of Wales. Getty Images

1997, English National Ballet Performance

A patron of the English National Ballet even after her divorce from Prince Charles, Princess Diana wore a sparkling blue minidress to a performance of Swan Lake in 1997. To complete the look, Diana wore a matching necklace and earring set of diamonds and South Sea pearls that she reportedly collaborated with luxury jeweler Garrard to make.

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Diana, Princess Of Wales. Tim Graham Photo Library via Get

1997, Christie’s Event In New York City

In 1997, Princess Diana worked with Christie’s in New York City to auction off 79 of her cocktail and evening dresses to benefit cancer and AIDS charities. Ahead of the auction, which raised $3.25 million, Diana attended a party in the city wearing a beaded floral print dress by Catherine Walker.

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Diana, Princess of Wales. Tim Graham Photo Library via Get

1997, Tate Gallery

The Tate Gallery’s 100th anniversary party also fell on Princess Diana’s 36th birthday, and she was gifted the perfect dress for the occasion—a black evening gown by Jacques Azagury, which included satin straps and hand-embroidered sequins and beads. To complete the look, Diana accessorized with a mix of sapphire and emerald jewels, including her emerald and diamond choker necklace.

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Paul Burrell and Diana, Princess of Wales. Getty Images

1997, in Bosnia and Herzegovina

While visiting with landmine victims in Bosnia and Herzegovina, Diana wore a pair of belted black jeans with a pale pink button-down shirt. The trip, which would mark her last official engagement before the Paris car crash that took her life later that month, helped to raise awareness around the need to ban the use of landmines.

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Diana, Princess of Wales. PA Images via Getty Images

1997, in London

In one of her most recreated off-duty looks, Diana wore an oversized mock-neck Harvard sweatshirt with black bicycle shorts as she jogged in London.

Princess Diana’s Most Iconic Style Moments

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𝗖𝗿𝗲𝗱𝗶𝘁𝘀, 𝗖𝗼𝗽𝘆𝗿𝗶𝗴𝗵𝘁 & 𝗖𝗼𝘂𝗿𝘁𝗲𝘀𝘆:
𝗙𝗼𝗿 𝗮𝗻𝘆 𝗰𝗼𝗺𝗽𝗹𝗮𝗶𝗻𝘁𝘀 𝗿𝗲𝗴𝗮𝗿𝗱𝗶𝗻𝗴 𝗗𝗠𝗖𝗔,
𝗣𝗹𝗲𝗮𝘀𝗲 𝘀𝗲𝗻𝗱 𝘂𝘀 𝗮𝗻 𝗲𝗺𝗮𝗶𝗹 𝗮𝘁