Celebrity Style

15 Photos That Show Diana's Style Evolution Over The Years

From her lavish wedding gown to her casual bike shorts.

Princess Diana was a versatile style icon, from her lavish wedding gown to her chic revenge dress to her casual cool biker shorts. See her best outfits, here.
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Princess Diana is the embodiment of timeless style. The late Princess of Wales was well known for her elegant approach to royal dressing. From floor-sweeping ball gowns to ultra chic column dresses, there was no royal affair that she didn’t steal the sartorial spotlight at. Catherine Walker, David Sassoon, Christina Stambolian, and Stephen Jones were just some of the British designers that Diana regularly collaborated with to create her most iconic high-end fashion moments, including her famous Revenge dress.

But it wasn’t all Cinderella gowns and Met Gala-appropriate attire. Princess Diana also knew how to go the commoner route and dress casually. In fact, more often than not, it was her everyday apparel that got people talking. During the 1990s, she was somewhat of an athleisure pioneer, wearing biker shorts with oversized sweatshirts to run errands. And, truth be told, while that exact look is now back in fashion — paging Hailey Bieber and Bella Hadid — no one can quite pull it off like Diana.

Without a doubt, Princess Diana was one-of-a-kind, which made her sudden death in 1997 that much more tragic and heartbreaking. Her legacy continues to live on through the charity work of her sons, Prince William and Prince Harry.

And as for Diana’s personal style, that too remains a source of inspiration for fashionistas everywhere. Royal family members including Kate Middleton and Meghan Markle frequently pay homage to Princess Diana with their ensembles.

Ahead, find Princess Diana’s total fashion transformation from her early years as a young princess in the ‘80s to her head-turning looks as a philanthropist and global jet-setter in the ‘90s.

1

May 6, 1981: Princess Diana’s Casual Countryside Look

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Ahead of their July 1981 wedding, Diana and Prince Charles spent time together in Balmoral, Scotland. The soon-to-be-princess wore an Inca jersey jumper with green corduroy trousers and Hunter wellies, and posed with their dog Harvey at the estate at Craigowen Lodge.

2

July 29, 1981: Princess Diana’s Wedding Dress

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Designed by the husband-and-wife team David and Elizabeth Emanuel, Princess Diana’s wedding dress was intricately embroidered with sequins and antique lace. She also wore a 25-foot train and a 153-yard tulle veil.

3

June 22, 1982: Princess Diana’s New Mom Green Dress

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When Prince William was born in London, Diana wore this emerald green polka dot print dress with a white bow across the front. She accessorized with red flats. The red color was poignant because it represents passion, love, power, and adventure, all feelings one might associate with becoming a new mom.

4

September 16, 1984: Princess Diana’s Second Baby Outfit

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At Prince Harry’s birth, Diana appeared in a long-sleeved red dress and gold bracelets. Perhaps as a nod to Prince William’s birth, she repeated the same red flats, which just emphasizes their significance in relation to her boys.

5

November 9, 1985: Princess Diana’s White House Gown

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During her visit to the White House, Princess Diana wore an evening dress designed by Victor Edelstein and showed off her dance moves with John Travolta. On the accessory front, she opted for a chic pearl choker.

6

June 29, 1988: Princess Diana’s Floral Frock

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At a charity polo match at the Guards Polo Club in Windsor, Diana stepped out in a vibrant floral dress by Bellville Sassoon. Matching blue heels completed her look.

7

July 27, 1989: Princess Diana’s Ballet Column Dress

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While attending a performance of Swan Lake by the Bolshoi Ballet at the London Coliseum, she wore a pink and white evening dress by Catherine Walker.

8

March 21, 1990: Princess Diana’s Yellow Skirt Suit

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While visiting a school for the deaf in Yaounde, during a three-day visit to Cameroon, she chose to wear a pink and yellow Catherine Walker suit with a hat designed by Philip Somerville.

9

July 22, 1991: Princess Diana’s LBD

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At a film premiere in London, Diana kept it classic in a little black dress designed by Bellville Sassoon. She finished the look with black teardrop earrings.

10

September 24, 1992: Princess Diana’s Fiery Red Ensemble

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She went for all-over red while attending the premiere of the film Just Like A Woman in London. A matching clutch and heels, plus a diamond necklace, created the ultimate glam moment.

11

March 1993: Princess Diana’s Ski Slopes ‘Fit

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During a skiing holiday in Lech, Austria, Princess Diana went for a red puffer jacket and fitted black leggings to hit the slopes. White mittens and ski boots topped off this sporty ensemble.

12

August 24, 1994: Princess Diana’s Biker Shorts

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Princess Diana was spotted wearing a pale blue sweatshirt, pink cycling shorts, and crisp white sneakers as she was leaving Chelsea Harbour Club in London. The tortoise sunglasses add a sophisticated touch.

13

November 20, 1994: Princess Diana’s Revenge Dress

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Diana wore a black, off-the-shoulder Christina Stambolian dress to attend a Vanity Fair party at the Serpentine Gallery in London. Why is it called the Revenge Dress? Because she wore it the same evening Prince Charles confessed to his longterm affair with Camilla Parker Bowles.

14

June 27, 1995: Princess Diana’s Halter Dress

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To attend a dinner at the Serpentine Gallery in London’s Hyde Park, she wore a pale blue halter-neck dress by designer Catherine Walker. She paired the look with a matching clutch and heels.

15

December 9, 1996: Princess Diana’s Met Gala Look

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At her only Met Gala appearance, Diana arrived at the Metropolitan Museum of Art in New York for the Costume Institute Ball wearing a navy silk, floor-grazing slip dress. She wore a matching silk robe and sapphire jewels.