Princess Diana in Christina Stambolian (1994)
Princess Diana wore the ultimate revenge dress in June 1994, on the same day that her ex-husband, Prince Charles, first openly discussed his relationship with Camilla Parker-Bowles.
The black strapless dress, made custom for Diana by Greek designer Christina Stambolian, made sure that the Princess grabbed all of the newspaper headlines on the following day and asserted her newfound independence from the British Royal Family.
Princess Diana in Versace (1995)
In the mid-'90s, Diana further asserted her independence by wearing more revealing gowns than she would have been allowed to wear as a royal. Here, she's pictured in 1995 wearing a white mini-dress by Gianni Versace, whose designs were considered daring at the time.
Mariah Carey (1997)
At the 1997 MTV VMAs, Mariah Carey's now-iconic skirt and crop-top ensemble carried plenty more meaning than you'd first expect.
The dress became synonymous with her split from her ex-husband, Sony Music executive Tommy Mottola, who'd had control over her image since she released her first album seven years prior. Therefore, the dress signalled an emancipation of sorts for Carey, and a departure from her family-friendly image.
Jennifer Lopez in Michael Kors (2004)
Jennifer Lopez's engagement to Ben Affleck provided tabloid fodder for three consecutive years, and the world was shocked when the relationship ended in January 2004. However, Lopez's risqué Michael Kors gown, worn to the 2004 Golden Globes, showed the world that she was doing just fine.
Jennifer Aniston in Chanel (2005)
Aniston was subjected to one of the prickliest splits in Hollywood history, when she and her then-husband Brad Pitt broke up, only for him to couple with his Mr. & Mrs. Smith co-star, Angelina Jolie, soon after.
However, following news of the breakup, Aniston had the perfect revenge moment when she wore this effortless Chanel dress to a red carpet event in October 2005.
Reese Witherspoon in Nina Ricci (2007)
Reese Witherspoon kept a low profile in the months following her split from her husband, actor Ryan Phillippe, in late 2006. Regardless, the actress resurfaced in January 2007 at the Golden Globe Awards, in a luminous gold strapless dress by Nina Ricci.
Bella Hadid in Alexander Wang (2017)
Gomez and The Weeknd attended the red carpet for their very first appearance as a couple, but it was Hadid who stole the show in this daring sheer catsuit by Alexander Wang.
Bella Hadid in Alexander Wang (2017)
While many thought Hadid couldn't go much racier than her Met Gala look, she proved that she could go much bolder (on the same night, no less). The supermodel continued her risqué streak with this entirely sheer black look, with only tape and underwear preventing complete nudity.
Selena Gomez in Jacquemus (2017)
After Gomez and her boyfriend, The Weeknd, split in October 2017, she sported a sultry look of her own. For a red carpet event in the same month, the actress and ex-Disney Channel star wore a bold black mini-dress by Jacquemus, helping launch the then-relatively small French label to global prominence.
Lady Gaga in Celine (2019)
In February 2019, news surfaced of Lady Gaga's split from her fiancé, Christian Carino, around the time that tabloids incorrectly speculated a romance was brewing between the performer and her A Star Is Born co-star, Bradley Cooper.
Only days after news of her split from Carino surfaced, Gaga attended the 2019 Grammy Awards in an edgy Celine by Hedi Slimane gown—a notable departure from the more conservative looks she donned during the 2019 awards season.
Irina Shayk in Versace (2019)
Following her unexpected split with her partner of three years, Bradley Cooper, supermodel Irina Shayk immediately continued her work obligations—one of which was walking at Versace's spring/summer '20 menswear show.
What followed was Shayk parading around Milan in an array of daring Versace looks, giving the impression that a breakup was the last thing on her mind.
Katie Holmes in Khaite (2019)
After the news surfaced of her split from actor Jamie Foxx in August 2019, Katie Holmes' first post-breakup look proved instantly iconic. In late August 2019, the actress stepped out in New York wearing a cardigan and matching cashmere bra by New York label Khaite, telling the world that despite going through a breakup, her summer was going swimmingly.