Chappell Roan attends the 2024 ASCAP Pop Music Awards at The Houdini Estate on May 08, 2024 in Los Angeles, California. (Photo by Emma McIntyre/Getty Images)

Chappell Roan is blowing up this year, from her commanding stage presence to leading the charts. The queer Missouri native, born Kayleigh Rose Amstutz, started her music career with heavy influence by ’80s synth-pop and early 2000s pop hits. Her debut album, 2023’s The Rise and Fall of a Midwest Princess, is an example of that “campy” sound.

Universal Music Group's 2023 After Party Celebrates The GRAMMYS, 6 of Chappell Roan's Wildest Outfits
(Photo by Rodin Eckenroth/Getty Images)

Roan auditioned for America’s Got Talent at 14 without success. Reflecting on her audition, she said, “I didn’t make it; I had no idea what I was doing.” Determined to make it in the music industry, she began uploading covers to YouTube under the name Kayleigh Rose, drawing attention from various record labels and fellow Queer icon Troye Sivan. After she uploaded her original song “Die Young,” Roan was quickly signed to Atlantic Records. In 2017, her debut EP, School Nights, featured the song.

While signed, the musician adopted the stage name Chappell Roan in honor of her grandfather Dennis K. Chappell, who died of brain cancer in 2016. His favorite song was the 1959 Western song “The Strawberry Roan” by Marty Robbins. She has also expressed dislike for her first name, Kayleigh.

Roan was dropped from the label in 2020 after the release of “Pink Pony Club” due to her poor-performing releases at the time. A few years later, in 2022, Roan released songs independently before releasing her debut album through Island Records in 2023. The album’s commercial breakthrough was helped by Roan’s supporting act spot on Olivia Rodrigo’s Guts World Tour, her performances at music festivals like Coachella and Governors Ball, and the success of her follow-up single, “Good Luck, Babe!”

Roan’s Style Inspiration

In a 2022 interview, the musician said she bases her aesthetic on what a pop star would have worn when she was a child in the early 2000s. “When I was little, I loved Bratz, the classic Barbie movies, Britney Spears, I was really into fairies and Spy Kids.”

During her recent appearance on The Tonight Show Starring Jimmy Fallon, Roan told the host what inspires her wild outfits while wearing a Black Swan-inspired look reminiscent of early Lady Gaga. Roan is known for her elaborate, avant-garde looks, so naturally, Roan said she and her stylist Genesis Webb pull looks from drag queens, horror movies, burlesque, and theatre.

“I love looking pretty and scary, or pretty and tacky — or just not pretty, I love that, too,” Roan told the host. The artist, who is a 20-something, adds that she doesn’t like to take it seriously. Watch the interview below.

Take a Look Below at 6 of Chappell Roan’s Wildest Outfits

  • Barbie Swan Lake

    While appearing on The Tonight Show Starring Jimmy Fallon, Roan changed from her Black Swan outfit to a white version with the same theme. Hauntingly beautiful, Roan’s look featured a white feather headpiece, looking very much like Angelina Jolie’s horns from Maleficent. The singer kept on her stiletto, pearl-colored nails that featured the cutest wispy tassels hanging from them to complete her “Barbie Swan Lake” look.

  • Club Kids Never Left Bitch

    Sharing photos from her performance at Tennessee’s Bonnaroo Music Festival, the artist wore an eye-catching yellow and teal set, making her look like she is made out of plastic. With hardware details in her belt and her top’s zipper, Chappell’s makeup was wild. With her face painted white, she drew on pencil-thin McDonald’s arch-shaped eyebrows, with stitch lines drawn across one of them. Her eyes were done in iconic drag style, with a smoky eye blended out with vibrant colors and a teal-hued blush to match the colors in her outfit.

  • Gov Ball Lady Liberty

    This is probably her most iconic look so far. While having her body painted in the same hue as the Statue of Liberty, Roan’s New York Gov Ball concert look had the artist tote Lady Liberty’s torch, wearing a crown and a dramatic cut-crease eye makeup. As campy as it gets, she emerged from a big apple in the Big Apple and toked up a huge joint while performing for the gigantic crowd, which packed the area as far as eyes could see. Roan told the crowd she was “in drag” as the monument because Lady Liberty is “the biggest queen of them all,” before quoting the poem etched on the Statue of Liberty.

  • Filth

    While attending Kentuckiana Pride, Chappell declared: “Filth is my politics! Filth is my life!” The singer-songwriter, whose entire look was an homage to groundbreaking drag performer Divine, wore a bright red bedazzled long-sleeve dress with a leopard-print bra peeking out. With teased, curly hair reminiscent of the ’80s, Chappell’s makeup featured classic drag style with bright pink cheeks, pencil-thin eyebrows, and a blue-hued cut-crease eyeshadow look with lush lashes. For her performance, she changed into a cheetah bodysuit with a matching choker.

  • Butterfly Queen

    In this glamorous, close-up photo of Chappell, she gazes into a handheld mirror in this gorgeous hot pink butterfly ensemble. With little baby pink lace butterflies on her hot pink arm sleeves, she paired the sparkling outfit with a bedazzled tiara. The artist wore butterfly-inspired eye makeup, with smoky black eyeshadow, dots at the corners like a butterfly’s wings and hot pink pencil-thin eyebrows with gems laid across the top.

  • Little Piggy

    Shading the Grammys for not inviting her to the annual awards ceremony, this “little piggy” shared photos of her attending an after-party and commanding all the attention with this look, which is the cover art for her single, “Good Luck, Babe!” Chappell wore a prosthetic pig nose in her red Renaissance-era-inspired outfit. For this look, the artist’s makeup was more neutral and her eyebrows looked natural as she sported a red lip to match her ensemble. Her red mesh veil sat atop her head, held up by horns. Her stylist said the mood board the artist created for this look included Gummo and director Chris Cunningham visuals, screen grabs from The Tales of Hoffmann, and Christina Ricci’s nose from the film Penelope.

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