Princess Diana's 27 Best Style Moments

No one could pull off bold shoulders and big hats quite like her.

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No one could pull off bold shoulders and big hats quite like her.

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The Tartan Dress

In January 1981, just before her engagement to Prince Charles, Princess Diana showed off her budding fashion sense in a twee tartan dress.

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The Engagement Dress

Like her son's fiancée decades later, Diana wore blue when she and Charles posed for their first official engagement pictures on February 1981.

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The Novelty Jumper

Shortly before their big day, Charles and Diana had a bit of down time on the Balmoral Estate. We love Diana's novelty jumper and corduroy trousers, wonderfully retro!

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The Wedding Dress

It was the dress that had everyone talking. The ivory silk taffeta gown, designed by David and Elizabeth Emmanuel, was decorated by hand with embroidery, lace, sequins, and 10,000 pearls. It also featured a whopping 25-foot train and was valued at the time at $14,050.

Just in case anything happened to it, there was a spare one made to avoid ruining the big day.

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The Honeymoon Suit

On honeymoon in Balmoral, Diana wore a suit designed by Bill Pashley to match Prince Charles' kilt.

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Ruffled Red Gown

While pregnant with Prince William, Diana dazzled in this Marie Antoinette-inspired dress by David Sassoon at a function at the Barbican Centre.

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The Post-Maternity Dress

We love this green polka dot number, which she wore as she left the Londo Wing at St Mary's Hospital with a tiny Prince William in 1982.

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The Drop-Waist Dress

The Princess made headlines in this vivid blue drop-waist gown by Bruce Oldfield.

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The Floral Skirt

The floral skirt, the white shirt, the jumper tied around the shoulders, the kitten heels… Diana was dressed perfectly for the polo in 1985.

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The Emerald Gown

On a trip to Australia in 1985, all eyes were on Diana as she danced with Prince Charles. Her blue ballgown was only made better by her diamond and emerald choker worn as a tiara.

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The John Travolta Dress

The iconic design by Victor Edelstein, worn by Diana as she danced with John Travolta at a White House dinner.

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The Red and Black Outfit

Always ready to push the fashion boundaries, Princess Diana wore this Murray Arbeid flamenco dress with one red glove and one black glove at America's Cup Ball in 1986 — '80s fashion at its best.

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The Wide Shoulders

Diana was often nicknamed "Dynasty Di" by the tabloids for her love of wide-shouldered gowns such as this one.

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The Military Suit

Diana had a longstanding relationship with fashion designer Catherine Walker, who dressed her from Prince Williams' birth to her death. This white suit with drum majorette gold frogging and epaulettes was created for her visit to the Sandhurst Military Academy in 1987.

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The Pale Chiffon Dress

Another stunning Catherine Walker design.

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The Floral Dress

We love this floral ruched dress worn to a Romeo & Juliet performance in London in 1989. It was one of her favorite designs and she wore it several times.

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The Pink Dress

Princess Diana looked breathtaking in this decadent pink dress by Catherine Walker at a banquet in 1989.

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The Pearl Dress

Perhaps one of her most iconic dresses, this high collar dress was inspired by Elizabethan ruffs and created by Catherine Walker for an official visit to Hong Kong. The Princess affectionately called it her "Elvis dress."

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The Oversized Hat

Not many people could pull off a huge hat, but Diana was one of them. We love the matching dress and accessories, too.

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Diana dressed to impress at a banquet in South Korea in 1992 in a Catherine Walker gown, which she accessorised with the Spencer family tiara.
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The Column Dress

Diana dressed to impress at a banquet in South Korea in 1992 in a Catherine Walker gown, which she accessorized with the Spencer family tiara.

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The Revenge Dress

This little black dress sparked a thousand headlines after Diana wore it to an event at the Serpentine Gallery. Designed by Christina Stambolian, it was dubbed "the revenge dress" because the Princess wore it the same day Prince Charles confessed to his affair with Camilla.

The designer said Diana was originally too scared to wear it, "She thought it was too daring."

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The Navy Dress

Her divorce from Prince Charles was a turning point for Diana, and her style reflected it. She wore bolder designs and had an edgier beauty look, going for slicked back hair and smoky eyes.

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The Christian Lacroix Dress

This Christian Lacroix number was the perfect outfit choice for a dinner in Paris in 1995.

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The Chambray Shirt and Chinos

Pictures of the Princess' visit to an Angolan hospital become a symbol of her involvement with charity work.

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The Pale Blue Dress

For a performance of Swan Lake at the Royal Albert Hall in 1997, Diana chose a simple powder blue frock by Jacques Azagury.

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The White Suit

Princess Diana wore a chic white suit to meet Mother Theresa in New York in June 1997.

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The Fitted Dress

Diana embraced more form-fitting designs in the late '90s, like this floral Catherine Walker dress, worn with Jimmy Choos in New York shortly before her death in 1997.

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