Rumer Willis' Most Tragic Hairstyles Of All Time

It's not easy being A-lister offspring. Demi Moore and Bruce Willis' daughter, Rumer Willis, knows that only too well. She was forced to grow up in the spotlight and was subject to intense media scrutiny over her looks. That's something that's not easy when you're going through your awkward teen years. And Rumer's were decidedly difficult, with her rocking some pretty dodgy hairdos while finding her groove.

Since entering adulthood, Rumer has gone through an extreme transformation. She's grown into a confident, beautiful woman and mom. Still, it's been a difficult journey that wasn't helped by constant comparisons to her mom. While Demi's daughter Scout could be her twin, Rumer has her own unique look. Sadly, some celebrity bloggers such as Perez Hilton decided Rumer didn't fit their beauty ideal and mercilessly mocked and derided her online. Not surprisingly, it had a massively negative impact on the young Rumer's self-esteem.

"It was really crazy, especially because I [moved to Hollywood] right at the peak of my awkward phase of trying to figure out who I was," she told HuffPost in August 2019. "... When you're 14, 15, I didn't really understand having value in myself yet." Thankfully, Rumer found her value. She also found her confidence and style. But she went through some pretty tragic hairstyles to get there; we're checking out some of them.

In early 2007, Rumer Willis threw caution to the wind, chopped her long locks off, and went a shade of deep, deep black. Taking her transformation a step further, she channeled a Las Vegas-era Elvis Presley with an updo quiff and sideburns. It was a bold new look, which is exactly what Rumer was aiming for. "I kind of just wanted to chop it off and try something different," she told People in April.

It was a big year for Rumer. In November, the Hollywood Foreign Press announced that she'd been chosen to be Miss Golden Globe at the organization's 65th award show. It's an honor that proves nepotism is still alive and kicking in Hollywood, as Bruce Willis and Demi Moore's oldest daughter followed in the footsteps of Don Johnson and Melanie Griffiths' daughter, Dakota Johnson, Kevin Costner's daughter, Lily Costner, and Clint Eastwood's daughter, Kathryn Eastwood. The HFPA scrapped Miss (and Mr.) Golden Globe in 2017, replacing it with Golden Globe Ambassador. Not because of blatant cronyism, though. Instead, they explained in a press statement, "The title has been changed ... to better reflect the role and express the inclusiveness that has always been central to the Hollywood Foreign Press."

Meanwhile, poor Rumer had to wait a year to grace the stage as the 2008 show was canceled due to the ongoing Writers' Guild of America strike.

In September 2007, Rumer Willis decided to see if it was true that blonds have more fun. No official word on whether she found the answer or not, but her curly blond mop top 'do could have seriously hindered her quest. Willis' hairstyle was a total '80s Madonna throwback, one that would best be forgotten.

Meanwhile, whether it was intentional or not, it was bleached a radioactive mix of orange and yellow, ripped straight from Donald Trump's hair hue book. Still, the 19-year-old was thrilled with her new look. Apparently, the color was intentional. Shockingly, it was also created by a professional hairdresser in a hair salon and not the result of a self-inflicted botched box job. Oh, and it took a whopping seven hours to complete.

"'Honestly, it just took a long time. I got there at like 1 [p.m.], and I didn't leave until 8 p.m. I have really dark hair, so it took a long time, but it didn't really hurt," Willis told People. "I got the idea because the movie I just finished, I was wearing a blonde wig, so I saw myself like that. And I just went for it."

By October 2007, Rumer Willis had ditched her blond Madonna mop and gone all in on a chestnut Richard Simmons-style coif instead. She debuted her new 'do at the Victoria's Secret Phi Beta PINK party in Beverly Hills, Califonia. It turns out that Rumer's change of color was more down to necessity than choice. She explained why she returned to the dark side in a December 2007 GQ Men Of The Year Awards red-carpet interview. "When you dye your hair blond, it tends to get a little ragged, so then I cut it off," Rumer told USA Today.

Even though she'd only turned 19 that year, Rumer was already well-versed in the ways of the pesky paparazzi. Still, that didn't mean she welcomed the unwanted attention. "I hear a lot that as soon as [young stars] put themselves out there, they're free game," Rumer told Access Hollywood in August. "It's kind of dehumanizing."

Talking of dehumanizing, Rumer admitted to Billy Bush that she endeavored to swerve gossip blogs whenever possible. Which, in addition to continually critiquing her looks, also accused her of cashing in on Bruce Willis and Demi Moore's celebrity. "There's obviously a lot of people that want to say that I'm doing some kind of train of my parents and that I have some big trust fund," she said. "And it's so easy to judge people and put them down when you're not looking at them in the face."

Rumer Willis brought the va-va-voom in December 2008 while attending the Stars for a Cause at The HFPA Salute To Young Hollywood Party at Nobu in Los Angeles. Her hair was a deep red Jessica Rabbit, and just like the cartoon vixen, it was set in soft waves. However, it was in that awkward limbo stage that hair suffers through while growing from short to long. Unfortunately, it resulted in a messy bob of different lengths. Still, Rumer's outfit was totally on point. She looked great in a V-neck LBD and knee-high boots.

2008 was a great year for Rumer, as she got to show off her acting chops in her first major movie role. The comedy romance "House Bunny" wasn't exactly a blockbuster, and the critical reception was decidedly lackluster — it scored a paltry 43% on the Tomatometer — but Rumer was psyched to finally be following in the footsteps of her famous folks, Bruce Willis and Demi Moore.

"I kind of grew up on [movie sets], so being able to [act] myself has been really amazing," Rumer told Female.com.au. "I've felt really lucky to do the few things that I have. It is a very different experience because there is a shift in your mindset when you go from being the accessory to being the one who's actually in front of the camera, so it has been a different kind of ride or journey."

Rumer Willis was rocking her natural curls when she was snapped out and about in Los Angeles in August 2022. She wore her locks long with bangs and dyed an unfortunate shade of orange reminiscent of Carrot Top, a look nobody really wants to go for unless they're Carrot Top, presumably.

2022 was a challenging year for Rumer and her sisters, Tallulah and Scout Willis. Their dad, Bruce Willis, announced he was retiring from acting in March after being diagnosed with aphasia. "This is a really challenging time for our family and we are so appreciative of your continued love, compassion and support," the Willises announced in a statement (via Variety). "We are moving through this as a strong family unit, and wanted to bring his fans in because we know how much he means to you, as you do to him. As Bruce always says, 'Live it up' and together we plan to do just that."

Rumer told Fox News Digital in May 2024 that she hoped Bruce's brave decision to go public with his condition would help destigmatize the debilitating disorder and help others. "I think if there's any way sharing our experience brings hope — whatever comes forward as a family — that can have an effect and bring any sort of hope, comfort to someone else experiencing that, then to me, that's ... everything," she said.