40 of Princess Diana’s Best Style Moments Through the Years

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princess diana best style moments

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Princess Diana was an undeniable force in fashion. From her quirky sweaters and casual ensembles to her stunning black-tie gowns that made you remember she was a real Princess. Decades later, we’re still seeing her sartorial choices influence designers, celebrities and current members of the royal family. See how impeccable the People’s Princess’s style truly as we take a look back at Diana’s best look of all time.

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November 1980

Not long after news broke that Prince Charles was dating Lady Diana Spencer, Diana left her apartment in a pinstripe maxi skirt, a high-collared blouse and a burgundy fair isle cardigan.

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March 1981

After her engagement was announced, Diana turned up at an event in Cheltenham, England, in a naval-inspired suit.

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June 1981

Diana stunned in head-to-toe red at the wedding of Nicholas Soames and Catherine Weatherall, the sister of the Countess of Strathmore and Kinghorne. Here, Diana is pictured with The Queen Mother and Princess Margaret.

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August 1981

A 20-year-old Diana waved goodbye as she left for her honeymoon with new husband, Prince Charles. She added an oversized ivory jacket and one of her iconic chokers to her long-sleeved floral dress.

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June 1982

While pregnant with her first child, Diana wore an emerald green dress and netted fascinator to the annual Trooping of the Colour.

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June 1982

Weeks before giving birth to her first child, Diana attended a polo match in London, wearing a green polka dot dress designed by Catherine Walker. Diana rewore the dress when she left the Lindo Wing after Prince William was born.

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November 1982

Mere months after giving birth to son William, Diana attended a banquet in a one-shoulder gown and a pearl choker.

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March 1983

Princess Diana wore a breezy, bright yellow sundress to visit school children in Australia. The long-sleeved and high-neck dress paired perfectly with the Princess’s white leather accessories.

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July 1983

On her second wedding anniversary, Princess Diana attended a polo match wearing a boat neck blouse with belted blue gingham pants.

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August 1983

Diana’s ’80s wardrobe can be marked by two things: patterns and sleeves. Combining both, the Princess dressed up a black and white blouse with a black leather wrap belt and a white pencil skirt.

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June 1984

Princess Diana’s maternity style only got better. One of her best looks when she was expecting Prince Harry was an ice blue satin evening gown with a drop waist silhouette.

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October 1984

What does one wear to the unveiling of a cruise liner named after you? Princess Diana opted for a coordinated suit and beret look.

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February 1985

Diana added a white-bibbed blouse and black boots to her long-sleeved, calf-length dress.

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April 1985

During her royal tour of Italy, the Princess wore a suit by one of her favorite designers, Catherine Walker, with a matching white cap.

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April 1985

While in Sicily, Diana chose another Catherine Walker ensemble with a pale pink hat.

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June 1985

At a polo match, Diana was stylish in a blue floral pencil skirt with a white blouse. She added matching red accents by way of her heels, belt, and sweater.

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October 1985

While working at home, Diana donned a silk polka dot dress, complete with a Peter Pan collar. The navy and white frock later served as inspiration for a look Kate Middleton has worn on multiple occasions.

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May 1986

During a trip to Japan, Diana stepped out in a satin blue evening gown, designed by Yuki Torimaru. She added a diamond and sapphire headband and a pair of drop earrings, which were a gift from the Saudi royal family made to match her engagement ring.

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June 1986

Diana watched Prince Charles play polo in a casual striped dress and large green leather belt.

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July 1986

While being photographed at her home in Highgrove House, Diana wore a pair of cropped pink gingham pants, a hot pink sweater, and white leather moccasins.

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July 1986

At an event at the German Embassy, Diana looked like the perfect princess in a white and gold strapless evening gown and tiara.

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May 1987

Wearing a strapless chiffon evening gown by Catherine Walker and aquamarine jewelry, Diana rivaled the best of Hollywood on the red carpet of the Cannes Film Festival.

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June 1987

Princess Diana paired a white pleated maxi skirt with a pair of metallic flats and a fun nautical sweater for a day out with a young Prince Harry.

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August 1987

On a holiday in Spain, the Princess donned a matching canary yellow shirt and pants. She broke the pieces apart with a thick gold belt.

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January 1988

Diana stunned in a floor-length red gown with a subtle hint of sparkle. Her best accessory? Her megawatt smile.

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May 1988

Diana proved that even a baseball cap, sweatshirt, and jeans can look chic.

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February 1988

In what could be a photo straight out of the pages of a magazine, Diana posed with umbrellas in Thailand in a gingham top and a white pencil skirt.

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February 1988

During an official visit in Bangkok with Prince Charles, Diana wowed in oversized shades and waist-cinching skirt and top.

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January 1989

Like Kate Middleton after her, Diana wasn’t afraid to wear the same outfit more than once. Both times she wore this Catherine Walker gown, she accessorized it with a large necklace that matched her sapphire engagement ring.

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March 1989

The Princess wore a bright pink and red Catherine Walker dress and Philip Somerville hat on an official tour of Kuwait.

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