These Celebs Took Fashion Risks With Their Funky Hats (& It Totally Paid Off)

In the world of Hollywood, what you wear on the red carpet and on the big stage matters. Some celebrities' worst nightmare used to be ending up on "Fashion Police" and getting blasted for wearing something that they didn't quite pull off. But a true mark of a star is one that doesn't shy away from taking fashion risks, but instead takes bold style choices to stand out. One way of doing that is to accessorize your look. As some Hollywood stars have shown us, the rule "less is more" doesn't quite apply to a funky hat.

The bigger and funkier the hat, the more memorable an outfit becomes in pop culture. Sometimes it pays off, and sometimes you may become one of the many celebs on the worst-dressed list at the Met Gala. The following celebs took a huge gamble on rocking these funky hats. Some looks started a trend and a few turned into memes. Either way, funky hats certainly paid off for these celebs.

John Travolta may have played stylish men on screen in movies like "Grease" and "Saturday Night Fever," but the actor in real life has always kept it simple. On the red carpet, Travolta is typically seen playing it safe with classic suits in simple colors. However, the star has recently made his directorial debut, and director Travolta seems to have a much different look.

At the 2026 Cannes Film Festival, Travolta premiered his directorial debut, "Propeller One-Way Night Coach." On his way there, the actor posted an Instagram video alongside his daughter, rocking a navy blue beret while speaking French. It wasn't just a prop for the cheeky video, as The Cut reported, the following day the actor rocked another beret, this time in cream. The accessory immediately became a viral moment.

Travolta was slightly shocked by the attention, but embraced the positive feedback on his new look. When asked about his new colorful accessories, he explained that he was paying homage to his new title as director. "I looked up pictures from the '20, '30s, '40s, '50, '60s, and the old-school directors wore berets, and the glasses, and I thought, 'That's what I'm doing. I'm doing an homage to being a director, so I'm going to play the part of being a director,'" the star explained to CNN.

Nowadays, it's hard to think of Zendaya as anything other than an actor in high demand and a fashion it-girl. Zendaya's stunning transformation from a child star to red carpet icon is partly due to the fashion risks she takes in collaboration with her stylist, Law Roach. One fashion risk in 2014 definitely turned into a meme, but, according to Zendaya, it paid off. At the 12th annual Teen Vogue Young Hollywood Party, Zendaya arrived wearing a sleek black Armani suit and paired it with an extra-large Emporio Armani hat, per Teen Vogue.

The look was instantly a meme online with many poking fun at the large hat, but Zendaya has since defended it. "I still see memes about this particular look," she said in an interview with Vogue in 2024. The "Euphoria" actor explained that she and Law Roach found the funky hat quite chic. "I would wear it again. Might have to bring it out of the archives one day." The memes weren't the only thing the hat has spawned — fans have even created a theory about it.

At the 2025 Met Gala, Zendaya wore another big funky hat to the red carpet, which fans speculated was a callback to the original 2014 hat moment. On TikTok, fans created the "Zendaya Hat Theory," which jokingly speculates that the star is hiding Tom Holland under her hats. It's a funky theory to match a funky hat.

Rapper, producer, and fashion icon Pharrell Williams can really do no wrong in people's eyes, even if he's rocking a large funky buffalo hat. At the 2014 Grammy Awards, Williams stole the show on the red carpet when he arrived wearing a vintage Vivienne Westwood hat, per CNN. Even though he walked away with the Record of the Year award for "Get Lucky" with Daft Punk, it was the "Buffalo Hat" that owned the night. That hat is (arguably) one of the first-ever viral celebrity hats (someone even made it a Twitter (now X) account), but the story behind it is pretty simple. "My friend Ronnie Newhouse bought it for me six or seven years ago," Williams explained to Vanity Fair. "It's so funny, because I wore it for an MTV interview then didn't wear it again for five years until I wore it the night of the [2014] Grammys."

The star eventually said goodbye to the hat. He auctioned the vintage hat off on eBay and got an impressive $44,100 for his charity, notes Rolling Stone. The buyer was none other than the American restaurant chain Arby's. Despite the online memes, the star continued to rock different colors of the beloved hat, and the look only solidified his place in fashion history. In fact, he was named CFDA Fashion Icon the following year, adds Fashionista. This funky hat certainly paid off.

After spending four seasons playing the high-strung Kendall Roy on "Succession," it's no surprise that some viewers had a hard time separating Roy from Jeremy Strong. In real life, Strong is much more bold with his fashion sense. Strong arrived at the 2025 Golden Globes rocking a green velvet suit, per Vogue. The bold color stood out on the carpet amongst traditional navy blue and black suits. For Strong, it wasn't just the color that stood out; it was the matching green bucket hat that he accessorized with. The funky hat garnered him plenty of compliments. While speaking with Entertainment Tonight on the red carpet, his look was compared to Hip Hop icons LL Cool J and Run DMC. "I'll take that," Strong replied with a smile. "I've been accused of only wearing brown, so I just thought, you know, that I'll just turn that on its head a little bit."

However, there was another star that felt like the look was familiar. The Princess of Genovia herself, Anne Hathaway, took to social media to let Strong know that he stole her look. "Sweetheart, I'm not mad you borrowed it but I didn't totally realize you were going to change the col... anyway, not important, congrats on your well deserved nom for The Apprentice," she wrote on Instagram, (via CNN). The funky hat may have become his signature look. W Magazine adds that he wore similar color-coordinated hats at other events, including the Cannes Film Festival.

When you think of '90s beauty, it's not long before the name Pamela Anderson will likely pop into your mind. Though she rocks a more toned-down, makeup-free look nowadays, the "Baywatch" actress was known for her incredible makeup and Pamela Anderson's gorgeous hair transformation. One look that lives rent-free in many people's minds is her red carpet look for the 1999 MTV Video Music Awards. Anderson walked the red carpet with then-husband Tommy Lee, rocking a fuzzy, feathered, and pink bucket hat. At the time, Anderson was no stranger to rocking large statement hats.

Just a few years prior, she wore a black, larger-than-life brim hat on the red carpet, per Fashionista. Though this look featured a much smaller hat, it was the one that caught everyone's attention. She paired the pink statement piece with a white corset and a bold, colorful makeup look that was peak '90s.

In an interview with The Hollywood Reporter, the designer, Ivy Supersonic, detailed how the look came to be. Supersonic was a frequent collaborator of Anderson's now-ex Tommy Lee. However, the designer explained that the look of the hat actually came from the actress herself. It quickly became a hit. "[Later] in 2003, Kelly [Ripa's] producer called me and said, 'Kelly wants to be Pam Anderson for Halloween. Could you lend Kelly a hat?'" Ripa wasn't the only one recreating the look. In 2024, the Queen Bee herself, Beyoncé, wore the exact look for Halloween, per W Magazine.

Rihanna has a long list of iconic red carpet looks, with most of them being on the Met Gala red carpet. Those daring looks make her a queen of that event. In 2018, she was rightfully named Co-Chair of the Met Gala. Per Vogue, the theme that year was Heavenly Bodies: Fashion and the Catholic Imagination.

The pop star sure looked heaven-sent in a Catholic couture look designed by John Galliano. The mini dress and extravagant coat put her on the Best Dressed list, but it was the bedazzled papal mitre (the traditional hats bishops wear) that made jaws drop. The hat was not a designer piece, but instead lent to Rihanna by a real cardinal.

According to Time, Timothy Dolan, the head of New York's Roman Catholic diocese, connected with the pop star for the final touch to her look. He confirmed that the viral hat was actually one from his personal collection. "She gave it back to me this morning... She was very gracious," the Cardinal revealed. Rihanna stole the attention on the red carpet and talked about the effort that was put into her look. "[The designers] beaded this by hand, and I just... it would be a sin not to wear it," she joked to Vogue.

Billy Porter's red carpet looks can never be seen as boring. The actor's fashion has always made headlines and caused discourse. In 2019, the "Pose" star made history by wearing a gown on the Oscars red carpet, with The New Yorker declaring that the look helped him "win the Oscars." It was only up from there, with more statement-making looks from Porter. The following year, just months before the world heard the words "social distancing," the actor took to the Grammys red carpet with a hat designed to block unwanted social interactions. Per Time, Porter wore a bedazzled blue wide-brimmed hat with a remote-controlled fringe that opens and closes to cover his face. "Get on my nerves, and the curtain closes!" he tweeted about his look.

Porter didn't cover his face the entire red carpet. While posing, the fringe repeatedly opened and closed, based on cues Porter gave his assistant who was holding the remote control. "We had a sign; when I stood in second position and clasped my purse between my legs, he was to press the button," Porter explained on The Tonight Show Starring Jimmy Fallon.

The inspiration for this look wasn't just the haters, but singer Billie Eilish. That same year, the singer donned a full beekeeper look to the American Music Awards. "It was so cute, and I said 'Oh that's really cute — but I'm never wearing something that covers up my face, I've waited too long for this moment,'" he explained. "Folks need to see my face."

Singer Erykah Badu isn't a stranger to large funky hats or eccentric fashion, and she's even known for her large collection of jaw-dropping hats. At the Soul Train Awards in 2017, the singer rocked a total of four large hats throughout the evening, per Harper's Bazaar. And as noted by Vanity Fair, in 2021, she attended the Met Gala wearing a large, funky top hat that felt very on-brand for her unique style.

But the hat that really sent things over the edge appeared in 2023. Vogue reported that the singer shut down Paris Fashion Week with an over-the-top hat. It had a large silhouette and a funky pattern that felt very, well, Badu-esque. Her signature head pieces, whether hats or head wraps, are all a part of a signature look. Luckily for Badu, she has never ended up with other celebs on the worst-dressed list at Paris Fashion Week.

Multi-hyphenate Lady Gaga worn some pretty outrageous outfits throughout her career. Who could forget the iconic meat dress? Interesting colors and bold patterns aside, there was one look that had a special meaning behind it. In 2016, the singer released her fifth studio album. For Gaga, this album took a more personal approach than her previous chart-topping work. "['Joanne'] is an album about my life without fame," she told SiriusXM. The album was named after Gaga's late maternal aunt, Joanne, whom the singer believes she is the reincarnation of. For this era, Gaga opted for a look that was much more reserved than she's typically known for.

On the album cover, her signature dramatic makeup and hair colors were absent, but she was wearing a large, wide-brimmed pink hat. The '70s-inspired funky hat was designed by Gladys Tamez, who told Billboard it took about eight hours to make. "She told me what she was looking for, and then she got really involved in the process. Pink is her favorite color, so we went from there," Tamez explained.

During that era, a team of designers made different versions of the hat for performances and events throughout the album's era, adding beads and even Swarovski crystals. Lady Gaga even pushed back against her stylist, who told her the hat didn't quite match every outfit. "'That's the point.' I said, 'This hat goes with nothing.' I said, 'This is Joanne,'" she told Women's Wear Daily.

There was no bigger story in 2016 than Beyoncé's highly anticipated album, "Lemonade." Just days before the singer was set to return to the Super Bowl halftime show, the singer surprise-dropped a new song, "Formation," teasing a new era. The visuals that accompanied the song featured Southern gothic backdrops, political references, and an oversized black wide-brim statement hat. The bold look was an immediate hit and a big departure from Beyoncé's past looks. Following the release of her deeply personal album revealing the truth about Beyoncé's marriage to Jay-Z, she went on a stadium world tour. The opening number for the show was none other than "Formation." The star appeared on stage in a similar wide-brimmed hat from the video, but it was even bigger.

In a behind-the-scenes video of the tour from Beyoncé's YouTube channel, her custom designer Marni Senofonte talked through the inspiration for the tour costumes and how they were connected to the antebellum looks featured in the "Lemonade" film. Senofonte revealed that the iconic large hats were hard to source. "Nowhere in the world do they make these hats," she said. "This hat maker literally drove to Mexico to buy sombreros." The following year, Beyoncé gave fans a chance to take home the iconic hat. According to Pitchfork, she auctioned off the 10-by-8-inch hat for charity. All proceeds were set to be donated to the Lung Transplant Project.