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Princess Diana's Best Fashion Moments

50 of Princess Diana's Most Iconic Style Moments

Princess Diana's Style: Prep School
Image Source: Getty / Tim Graham

Princess Diana's iconic style moments have influenced the likes of royals Kate Middleton and Meghan Markle, who have only followed in her footsteps, taking notes from her rulebook as to classic prints, sophisticated silhouettes, and inherited family jewelry reserved for specific occasions. From fashion spectacles such as her Elizabeth and David Emanuel wedding gown — featuring pouf sleeves and a 25-foot long train, and inspiring the replica Kristen Stewart wore in Pablo Larraín's 2021 film "Spencer" — to her iconic Christina Stambolian "revenge dress," Diana's wardrobe will be admired for years to come.

HBO's new documentary "The Princess" spotlights many of the times Diana's outfits were in the spotlight. "She's wearing diamond drop earrings lent by her mother. You want her shoes?" a reporter says excitedly during a live forecast from Diana and Charles's wedding at Buckingham Palace in 1981. "We should all be able to wear wedding dresses and celebrate!" a woman in the crowd gushes, as others are shown obsessing over the intricate details of the bridal look. The documentary footage emphasizes just how much importance was placed on the clothing choices made by the Princess of Wales, which is why all 50 of these appearances will go down in history, sporadically inspiring designer replicas, such as the famous red, white, and black sheep jumper she wore to a polo match in 1983, clad with a prim bow collar.

Ahead, scroll through Princess Diana's most-talked-about gowns, day dresses, sweaters, skirt suits, and trousers.

Additional reporting by Randy Miller

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