Princess Diana
Known as the "Revenge Dress," the LBD the Princess of Wales wore to the Serpentine Gallery's June 1994 party will go down in history. Diana wore the Christina Stambolian creation, considered risque at the time, the same night Prince Charles' tell-all interview was aired about their broken marriage and his affairs.
Reese Witherspoon
Fresh off her divorce from Ryan Phillipe, the Big Little Lies star shut down the 2007 Golden Globes red carpet in a stunning, yellow Nina Ricci mini that will go down in Best Dressed history.
Bella Hadid
Is there a day when the model doesn't look like a 10? Nope. Still, on Nov. 10, 2016, when Bella and ex The Weeknd split, she was spotted in a beige body-con dress with a thigh-high slit and sneakers. Pretty casual, right? A few weeks later, the former lovebirds reunited at the Victoria's Secret Fashion Show, where the singer performed and Bella was strutting down the runway, oozing sex appeal.
Anna Faris
Get it, Anna! The actress stunned in magenta Marc Jacobs at the 2017 Emmys, her first appearance since splitting with Chris Pratt.
Angelina Jolie
The original Tomb Raider actress' first appearance after splitting with Brad Pitt was a strong one, stylistically speaking. Joined by all her children, Angelina donned a lace black dress to the premiere of First They Killed My Father, which she directed and co-wrote, in Siem Reap, Cambodia.
Demi Lovato
After six "loving and wonderful years together," Demi split with then-boyfriend Wilmer Valderrama back in 2016. The "Sorry Not Sorry" singer appeared strong, smiley and like a silver siren at a UFC fight the day after announcing their split.
Katy Perry
The "Firework" singer attended the 2017 iHeartRadio Music Awards with a newly chopped head of hair, days after her March 2 breakup with Orlando Bloom. While she debuted her new look on Instagram, she wore a strapless, glittering August Getty jumpsuit to complement her fresh tresses.
Kaley Cuoco
The Big Bang actress looked her most casual-yet-put-together best the day her divorce to Ryan Sweeting was finalized, wearing a winter white coat and sneakers on the way into The Late Show With Stephen Colbert.
Gigi Hadid
It was the breakup that shook the fashion world...except the style remained impeccable, of course. Just a few days after announcing their split, the model was spotted on the chilly streets of NYC wearing a bold red turtleneck, windbreaker and plaid pants. Basically, winter wardrobe goals.