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8 of Chappell Roan's Craziest Outfits

chappell roan craziest outfits
Source: MEGA; @chappellroan/Instagram

See some of Chappell Roan's wildest costumes that have highlighted her unique and bold fashion sense.

April 18 2025, Published 12:05 a.m. ET

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67th Annual Grammy Awards

chappell roan craziest outfits
Source: MEGA

Chappell Roan won the Best New Artist award during her first-ever Grammy Awards appearance.

On February 2, Chappell Roan turned heads at her first-ever Grammy Awards appearance in a vintage Jean Paul Gaultier spring 2023 couture gown. She completed the avant-garde look with dramatic makeup featuring voluminous lashes and sharply arched eyebrows.

The "Pink Pony Club" singer successfully brought home the gramophone for Best New Artist after earning six nominations at the ceremony.

In her speech, Roan urged the music industry to provide better healthcare to artists and performers.

"I told myself, if I ever won a Grammy and I got to stand up here in front of the most powerful people in music, I would demand that labels in the industry profiting millions of dollars off of artists would offer a livable wage and healthcare, especially to developing artists," she said.

Roan, who revealed she was first signed onto a record label as a minor but was later dropped, added, "Like most people, I had a difficult time finding a job in a pandemic and could not afford health insurance. If my label would have prioritized artists' health, I could have been provided care by a company I was giving everything to."

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'Olivia Rodrigo: GUTS World Tour' Premiere

chappell roan craziest outfits
Source: MEGA

She went viral after a confrontation with a photographer at the time.

The 26-year-old "My Kink Is Karma" songstress supported Olivia Rodrigo at the Los Angeles premiere of Netflix's Olivia Rodrigo: Guts World Tour film on October 25, 2024.

Roan arrived in a sheer, form-fitting red dress adorned with dark red flowers that complemented her heavy makeup. She finalized her dramatic look with a pair of sheer gloves and black boots.

She made headlines after confronting a photographer who allegedly disrespected her at a Grammys party.

"You yelled at me at a Grammy party," she told the photographer, who was not visible in the viral videos. "I remember. You were so rude to me. And I deserve an apology for that … You need to apologize to me."

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2024 MTV Video Music Awards – Arrivals

chappell roan craziest outfits
Source: MEGA

Chappell Roan also scored the Best New Artist award at the 2024 ceremony.

Roan graced the 2024 MTV Video Music Awards red carpet event in a flowing sheer gray and maroon dress. She also wore accessories, including a cross necklace, a casual sword and silver jewelry.

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2024 MTV Video Music Awards Arrivals – Show

chappell roan craziest outfits
Source: MEGA

Chappell Roan was all smiles as she accepted her award.

The "Red Wine Supernova" singer was a showstopper in a stunning Rabanne Spring 2024 dress, featuring a metallic-style headpiece and a pair of matching heels.

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Lollapalooza Chicago 2024

chappell roan craziest outfits
Source: MEGA

Chappell Roan stood out in the crowd in her bright-colored costume.

Roan embodied a stunning wrestler on the Lollapalooza Chicago 2024 stage, wearing a pink, blue and silver latex leotard with a matching leather mask. She also cinched her waist using her colorful championship belt.

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Universal Music Group Awards After-Party

chappell roan craziest outfits
Source: MEGA

The singer is known for speaking out on social media.

At the Universal Music Group Awards after-party, Roan revived her "Good Luck, Babe!" art photo look by slipping into a custom red dress with a matching headpiece. She amped up her look with a prosthetic pig nose.

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Pride 2024

chappell roan craziest outfits
Source: @chappellroan/Instagram

Fans said Chappell Roan channeled She-Hulk at the time.

In a June 2024 carousel of photos, Roan shared her snazzy look with her body painted green by stylists. She also had long green hair and dramatic makeup in the snapshots.

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Pretty in Red

chappell roan craziest outfits
Source: @chappellroan/Instagram

Chappell Roan showed off her red and white outfit.

"just dug this dusty b---- up d--- we have come a long way girls 💋," she captioned a photo of herself in a flamboyant red and white costume.

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