The most daring revenge dresses of all time: From Princess Diana to Lily Allen


Princess Diana was the queen of the 'revenge dress' when she made headlines in 1994. See the A-listers who have followed in her footsteps.


A split image of Princess Diana and Lily Allen wearing black dresses
November 27, 2025
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Back in 1994, Princess Diana made history when she stepped out at the Serpentine Gallery, just after it was publicly revealed that her former husband, King Charles, had been unfaithful to her. She marked the occasion, the best way she knew how - with a killer fashion moment.

The dress in question was a daring black velvet off-the-shoulder creation by fashion designer Christina Stambolian, which the royal paired with sheer tights, a decadent triple pearl choker and a pair of killer stilettos.  

© Getty Images
Princess Diana's revenge dress was one of the biggest fashion moments in history

Little did Diana know then that moment alone would not only secure her place in fashion and cultural history but would empower generations of women to come. 

Since then, A-listers alike have taken a leaf out of Diana's book when heartbreak hits, proving that a misbehaving partner is no reason to hide in the shaddows.

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© Getty Images

Lily Allen

Case and point? Lily Allen. The British singer, who recently revealed her husband's alleged unfaithfulness in her chart-topping album West End Girl, channelled her inner Diana when she stepped out at the 2025 CFDA Awards in a sultry ensemble that was sure to turn heads

A little over a week after releasing the record, Lily made a surprise appearance at the 2025 CFDA Awards in a sultry ensemble that was sure to turn heads. The outfit in question was an ensemble from Colleen Allen. 

The look consisted of a barely-there bra top and matching slip skirt, completed with a flowing cape coat that the singer draped over her arms.

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© Dave Benett/Getty Images

Lily had another revenge dress moment last week while attending the 16Arlington x Antony Price fashion salon last week. Lily's Breakfast at Tiffanys-style gown bore so many similarities to Diana's aforementioned strapless gown, including the figure-hugging style and luxurious black velvet material. The 40-year-old singer's gown featured a dramatic slit and was paired with white satin heels. 

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© Getty Images for Vogue

Nicole Kidman

Another recent A-list revenge dress came from the Australian actress Nicole Kidman. In the wake of her September news that she and her then-husband, Keith Urban, were getting a divorce, the Big Little Lies star, 58, was every inch the timeless Hollywood star in a spellbinding Chanel number for the Vogue World: Hollywood event.

Nicole's designer number was a play from Diana's playbook, the dress in question, black and figure-hugging, although the actress's gown featured a strapless neckline and was adorned with a giant flower embellishment.

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© Ron Galella Collection via Getty

Elizabeth Hurley

The British model and actress Elizabeth Hurley did not play around when she attended the anniversary party for Valentino Garavani in 2000. The outing came in the wake of a cheating scandal with her ex-boyfriend, Hugh Grant, with whom she had recently parted ways.

Drawing a line under the ordeal, Elizabeth slipped into a slinky champagne-hued gown that featured a super-plunging neckline and waist-cinching cut-out panels.

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© Patrick McMullan via Getty Image

Jennifer Aniston

Following her very public split with fellow Hollywood actor Brad Pitt and subsequent relationship with Angelina Jolie, Friends star Jennifer Aniston brushed the scandal off her perfectly tanned shoulders and stepped out at the premiere of her movie Derailed in 2005. The film star dazzled in a glittering golden gown by Chanel that lit up the red carpet.

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© Ron Davis

Mariah Carey

Award-winning pop star Mariah Carey had her own Princess Diana moment in 1997. After splitting from her husband and manager, Tommy Mottola, the famous pop superstar arrived at the MTV Video Music Awards in a skimpy two-piece from Calvin Klein. The sultry set perfectly showed off Mariah's impeccable physique and marked a whole new era for the singer.

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