The Wildest Outfits Worn By Chappell Roan

Chappell Roan's debut album, "The Rise and Fall of a Midwest Princess," was released in September 2023. Over the ensuing year, the "HOT TO GO!" singer — real name Kayleigh Rose Amstutz — has become one of the entertainment industry's fastest-rising stars, exploding onto the cultural consciousness thanks to her inescapably-catchy hits and her transformative fashion. She's also grabbed headlines thanks to her openness about how difficult it is to suddenly be famous.

Roan told The Face, "I feel like fame is just abusive. The vibe of this — stalking, talking s*** online, [people who] won't leave you alone, yelling at you in public — is the vibe of an abusive ex-husband. ... I didn't know it would feel this bad." (Along those lines, she also cursed out a photographer on the VMAs red carpet, but if we're being honest, that one was quite justified.)

Controversy, fashion, and undeniably great pop music? Sounds like an icon in the making! The "Femininomenon" has upped the ante with each new stage show, dressing up in some wild, outrageous looks in her so-far-short career. Through it all, she's made sure to pay homage to the artists that inspire her, as she told Jimmy Fallon on "The Tonight Show." The "My Kink is Karma" singer explained, "We pull from drag, we pull from horror movies. We pull from burlesque, we pull from theater. I love looking pretty, and scary, or like pretty and tacky ... or just not pretty! I love that too." Safe to say that her fans love it, too. These are the wildest outfits worn by Chappell Roan.

When Chappell Roan performed at the Governor's Ball in New York City, she decided to pay homage to the location by coming out onstage inside a big apple. The "Naked in Manhattan" singer emerged from the giant fruit dressed as the Statue of Liberty, her entire body painted in green glitter, complete with a sparkling silver crown. While fans were gagged by the look, Roan herself was particularly pleased by how things turned out. "I've never felt this high in my life performing in the big apple as lady liberty herself," she wrote on Instagram. "thank you times a million [Governor's Ball] for everything and the unbelievable support from my team and the community surrounding me."

The outrageous look provided the perfect costume for Roan to deliver an important message onstage, too. After reciting "The New Colossus," the poem inscribed at the base of the statue, Roan added, "That means freedom and trans rights. That means freedom and women's rights" (via Rolling Stone). In reference to the Israeli-Palestinian conflict, she added while choking up, "It especially means freedom for all oppressed people in occupied territories."

During her Governor's Ball set, Roan also revealed that she had turned down an invitation to perform at the White House. "We want liberty, justice and freedom for all," she said (via NBC News). "When you do that, that's when I'll come."

For her performance on NPR's "Tiny Desk" series in April 2024, Chappell Roan chose an avant-garde look that referenced the album cover for "The Rise and Fall of a Midwest Princess." While certain elements were similar — a powdered white face, a red lip, a tiara — everything was dialed up to the next level for "Tiny Desk." The red wig piled atop her head was bigger than ever, and into it she'd stuck butterfly clips and crushed cigarettes. Her face was a starker shade of white, and this time her dress was pink instead of blue. Her stylist, Genesis Webb, told Vulture, "I wanted it to be very her so that when people saw it, it still fit in that iconography but also just pushed a little bit more."

There was another inspiration for the look, too: "RuPaul's Drag Race: All Stars" winner Alaska's devious puppet sidekick, Lil Poundcake. Roan is a noted lover of drag, and the iconic foulmouthed doll is a recurring joke across the hit reality competition franchise. In her interview with Vulture, Webb referred to the pint-sized character as a drag queen herself, explaining, "People were saying she resembled drag queen Lil Poundcake, which it looks exactly like. I wanted to do Lil Poundcake for Halloween in 2020, so that was clearly in the depths of my mind."

Throughout Chappell Roan's meteoric rise to superstardom in 2024, fans have pointed to several key inflection points that took her fame to the next level. Fans have circulated several graphs throughout the year showing her exploding number of monthly listeners on Spotify. One such event, as noted on a chart shared to Reddit, notes her April 12th and 19th sets at Coachella as important moments when the world took notice of Roan.

At the iconic music festival, Roan performed with her trademark powdered whitened face and massive mane of red hair. In addition to a jewel-encrusted choker and a leather cuff, Roan wore a cutout t-shirt reading, in big block letters, "EAT ME." Her stylist Genesis Webb told Vulture that the look was a reference to Paris Hilton's infamous "Eat the Rich" shirt. However, Webb told the outlet that fans shouldn't read too much into the message of the tee. "It was just funny. It was truly not a statement at all — literally having fun," she said. "I think it's very tongue in cheek."

As with many other Chappell Roan outfits, this one also paid homage to the drag community. In addition to noting that the studded necklace belongs to "RuPaul's Drag Race" winner Violet Chachki, Webb added, "Everything we do, I ask myself, 'Can this be on 'Drag Race?”"

In August 2024, Chappell Roan added to her list of iconic festival outfits when she dressed as a pink and blue luchador for Lollapalooza. The costume paid homage to the Mexican wrestling tradition of lucha libre, outfitting the "Super Graphic Ultra Modern Girl" singer in a metallic blue mask that went perfectly with the pink star on her wrestling belt. Roan was emotional as she took the stage in Chicago, later explaining on Instagram, "I was crying as I walked on stage at [Lollapalooza] because of the overwhelm of support. Thank you thank you thank you ... I will remember this forever."

The eye-popping look caught the attention of a number of real-life wrestlers, many of whom reacted to the fashion statement on social media. "Hi [Chappell Roan]!" Willow Nightingale, who wrestles for AEW, tweeted. "If you ever want to come to a wrestling show, you're always welcome at [AEW]." AEW wrestler Nyla Rose, on the other hand, wanted to see Roan in the ring, not just at the ring. "Aye [Chappell Roan]," she wrote, "you trying to fight."

Fans on the Chappell Roan subreddit noted an even deeper meaning to the singer's outfit choice. "It's been a thing for a long time," one fan commented, pointing to a long tradition of queer-coded wrestlers in Mexico. "Theyre called 'exóticos.' They wrestle in drag and are still popular today." 

It's no secret that Chappell Roan loves the art of drag. Upon accepting the award for Best New Artist at the 2024 VMAs, she expressed her gratitude to the queer community that she's proudly a part of. "I dedicate this to all the drag artists who inspire me," she said, wagging her finger appreciatively at the audience. "I dedicate this to queer and trans people that fuel pop."

Naturally, Roan paid homage to one of the most iconic drag queens of all time, Divine, a few months earlier. Divine made a name for herself as the star of such John Waters' films as "Hairspray" and "Pink Flamingos," shocking audiences with her bawdy performances and cementing herself a place in pop culture history. While performing at Kentuckiana Pride in 2024, Roan wore several looks reminiscent of some of Divine's most famous outfits. Her arched eyebrows and cigarette paired perfectly with the shape-hugging red dress from "Pink Flamingos." She then shed the dress for a leopard-print number inspired by Divine's instantly-memorable look from "Female Trouble."

"i like to believe madame divine was watching over the performance," Roan wrote on Instagram alongside a slideshow of photos of herself dressed as the "Lust in the Dust" star. "divine if you are reading this from heaven...come down and haunt me sometime xoxo."

In February 2024, Chappell Roan performed on "The Late Show with Stephen Colbert." With her first big televised performance falling on the day after Valentine's Day, she and her stylist, Genesis Webb, decided to make a statement. They put together a whimsical, old-fashioned, corseted look inspired in part by the film "Poor Things," an artistic, gender-flipped "Frankenstein" tale about a woman coming into her power. "In the brothel scene, all of the girls come out and they're very stylized in these lingerie-looking outfits," Webb told Vulture. "Chappell said she loved it too."

Putting the look together required a visit to a Los Angeles costume shop called Palace. Webb was able to source a number of vintage, archival pieces to combine for the look, only purchasing the petticoat new. "They just have so many amazing antique corsets, and these things are legitimately from — I mean, Chappell's is probably from 1910," she said. "It's all antique styling."

The performance stands out because it kickstarted Roan's incredible year, and it was a learning curve for both performer and stylist. "It was the first time that I had traveled for a job," Webb recalled. "Figuring out how to take care of these antique pieces in a suitcase, I was like, 'What is happening?' I just said a little prayer, checked the bag, and hoped for the best."

In early February 2024 — before her career really took off — Chappell Roan made a major fashion statement on the red carpet of the Universal Music Group Grammys after-party. "This little piggy went wee wee wee all the way to the after party bc she was not invited to the actual Grammys," she revealed on Instagram. Her vibrant red look included a headpiece reminiscent of an escoffion, a medieval headdress, which she paired with a black necklace.

The centerpiece of the look, however, was a prosthetic pig snout. Speaking with Vulture, stylist Genesis Webb declined to explain the thinking behind the wild fashion statement. "We were grappling with a lot of different ideas," Webb recalled. "I don't know if it's my secret to tell why she chose it," she continued. "That one felt right for a variety of reasons."

This was just an after-party, and Roan didn't like that the look didn't get the attention it deserved. She later wore it on the single cover for "Good Luck, Babe!" ensuring that the pig nose would be part of her burgeoning iconography. "She wanted it to be seen again," Webb said, "and now it's on a billboard in Times Square." Fans on Reddit were baffled by the nose, with one joking, "I like the theory that somebody on her team made a joke about the babe in Good Luck, Babe! being Babe the pig from the Babe movie, and she ran with it."

By the time Chappell Roan performed at the Hinterland Music Festival in Iowa, which took place in August 2024, she'd made quite the name for herself as a pop star known for her outrageous fashion choices. The only problem? She didn't have an outfit ready for this particular festival performance. Stylist Genesis Webb tried to assemble a group of nun costumes for Roan and her band to wear, but they hadn't arrived in time for Roan to hit the stage. Instead, she turned to a local costume shop called The Theatrical Shop. Owner Debbie Swander told Iowa Public Radio, "The fact that somebody wants to do a show and they're in a bind and they don't know where to turn... I mean, how could I not respond?"

Roan's team rented the nun outfits they needed, and the next day, Roan performed in full habit. The performance was on a Sunday, which certainly fit the theme. "I dedicate this next song to my ex," Roan said, introducing her "My Kink Is Karma" track, "who literally said I was an 'ungodly woman.' How do you like me now?"

On Instagram afterwards, Roan posted a slideshow of photos of herself and her sister sisters. In the caption, she pointed out yet another fitting reason why she would dress as a nun. "My church," she wrote, "is Chappell."

When Chappell Roan performed on "The Tonight Show with Jimmy Fallon," she wore two separate, complementary looks that told a story. First, while sitting next to Fallon for the interview, Roan wore a black feathered outfit that made her look like a giant bird. Then, for a stunning performance of "Good Luck, Babe!" at the piano, Roan wore a white feathered dress and curly blonde hair. Her typical white-faced makeup looked extra chilly, paired with icy blue eyeshadow and wine-stained red lips. On Instagram, she summed up her inspiration succinctly, writing simply, "barbie swan lake!!"

Genesis Webb, her stylist, went into more detail in an interview with The New York Times about the ensembles, which took months to pull together. The performance look included a tutu of sorts, and the bodice was encrusted with pearls. While swans are typically considered beautiful, the Chappell Roan look aimed for something else entirely. Webb explained, "It doesn't look like, 'Oh, a pretty swan.' It looks scary, almost like it could be in a horror film."

The makeup alone took two hours to perfect. Makeup artist Andrew Dahling told the outlet, "To a normal person, the extremity of it, the pain and the inconvenience of it all would have just been annoying." But Roan and her team are nothing if not determined. "Whatever it takes to get the look, we're into it," Dahling said.

As Chappell Roan's career has taken off, she's covered several magazines, each in a wild look. Arguably the most out-there look of the bunch is her Paper magazine cover, which makes sense when you consider that the magazine is known for its bold photoshoots. (Most iconically, they were the ones behind Kim Kardashian's "Break the Internet" photoshoot that focused on her legendary derriere.)

For Roan's Paper Magazine shoot, she dressed in a simple black bra and a yellow lace slip. That wasn't the focal point, though; instead, the look is all about that towering wig atop the singer's head. Against the stark white of the magazine's title font, the yellow leather duck-shaped Coach handbag stuffed into Roan's hair really catches the eye. On Instagram, she described her reaction to the cover, writing, "Thank you [Paper magazine] for having me. I appreciate nothing more than seeing myself and being jump scared."

In the accompanying interview, the Midwest Princess described her approach to fashion — at least, as it stood in the summer of 2024, as things were still exploding around her. "I am not trying to be a chic b****," she said. "I love the chic b****es, but I am not trying to be like that. Nothing turns me off more than frickin' luxury brands." Does Coach not count? Was that shade?

An unforgettable VMAs performance can cement a rising pop star as a force to be reckoned with. Think Britney Spears gyrating with a snake to "I'm A Slave 4 U," or Lady Gaga dripping blood as she was hoisted above the crowd to "Paparazzi." At the 2024 VMAs, all eyes were on Chappell Roan, who had spent the year delivering knockout performance after knockout performance. What would she do?

Roan's VMA domination began on the red carpet, when she turned up in a medieval-inspired look, complete with a flowy gown, massive cross necklace, a knight by her side, and even a sword, which she carried like it was any other old fashion accessory. That was the first of three looks; next came her "Good Luck, Babe!" performance look, which saw the singer outfitted in a full-on chainmail suit of armor, her hair in a long braid. This time she wielded a crossbow, setting the stage on fire as she wailed out the smash hit. Finally, when she won the award for Best New Artist, Roan capped off the night in a stunning, body-hugging chainmail dress by Rabanne.

John Shearer/Getty

Roan's makeup artist, Andrew Dahling, spoke with CNN about the team's inspiration behind the looks. "[What] if Joan of Arc was a glamour girl," he said. "It's very romantic. But sort of dark romantic. ... Very heavy on the eyes, very glowy skin, very ethereal." One thing's for sure: She looked Femininomenal.