Princess Diana’s Fashion After Separating From Charles Was Daring AF

Revenge is best served cold, but Di made it hot.

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All the recent talk of royal fashion serves as a reminder that the royal family’s biggest fashion It Girl will always be the late Princess Diana. Her looks were legendary, especially after separating from now-King Charles III, and her ‘fits are still referenced by royalty and A-listers alike.

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Princess Diana’s post-Charles style was largely defined by its rejection of the unwritten, but oft-mentioned, royal family's fashion rules. Join me on a stroll down memory lane through photos of Princess Diana’s most daring fashion moments as a separated wife and later divorcée.

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October 1992

The year Princess Diana and King Charles III announced their separation was the year Di stopped playing by the royal fashion rulebook. The strapless gown she wore to the Royal Gala Premiere of 1492 - Conquest of Paradise showed lots and lots of skin by royal standards.

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June 1994

Princess Diana wore her iconic “revenge dress,” designed by Christina Stambolian, to a dinner on June 29, 1994. While she was serving legs for days, clavicle, and décolletage, her then-husband was admitting to adultery on national television. Guess who came out on top that evening.

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November 1994

At a UNESCO charity event at Versailles in 1994, Princess Di continued to live her best life beyond the confines of royal fashion etiquette. Her Catherine Walker halter-neck evening gown showed her shoulders and a touch of cleavage, both of which are royal no-nos.

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January 1995

Princess Diana arrived at the CDFA Awards with slicked back hair and a sapphire in the center of her necklace. Her sleek, curve-hugging Catherine Walker gown sparkled as she took to the stage to present Harper’s Bazaar’s then-Editor-in-Chief, Elizabeth Tilberis, with a special award.

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June 1995

‘95 saw Princess Diana experimenting with much shorter hemlines. It appears that once Diana discovered halter dresses, she wasn’t about to let them go. This beaded Catherine Walker number also features a deeply (for Di) plunging neckline.

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November 1995

Princess Diana went full va-va-voom for a dinner she attended in Argentina. The lace dress was short, the monochromatic styling was in a bold, suggestive color, and the velvet ribbon detail on the neckline drew the eye to Di’s décolletage.

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October 1996

Two months after she and Charles divorced in August 1996, Princess Di went one-shouldered at a gala in Sydney, Australia. This Versace satin gown was a new look for Diana, proving that single life had turned her into a bit of a fashion risk-taker.

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December 1996

In ‘96, the Met Gala was celebrating the 50th anniversary of Dior and Princess Diana arrived in her most scandalous look to date. Her floor-length, lingerie-inspired gown was designed by none other than John Galliano.

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June 1997

In 1997, Princess Diana decided to auction off 79 evening gowns from her former married life. For the auction and its gala, the former HRH (Her Royal Highness) wore a short, beaded dress, a pair of matching heels, and a big smile as she bid farewell to one chapter of her life and prepared to open a new one.

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June 1997

‘97 was the year the world lost Princess Diana. In one of her final public appearances, a performance of Swan Lake at Royal Albert Hall, Diana looked radiant in an aqua Jacques Azagury dress and a pair of Jimmy Choos.

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