Chappell Roan’s Best Outfits Through the Years

Yes, we’d like to take all of these looks hot to go, please and thank you.

Allie Hayes | Dec 24, 2025

Chappell Roan / Nina Westervelt/Billboard via Getty Images

When we think of standout style in modern music, we think of Chappell Roan—and for good reason!

The 27-year-old singer-songwriter first broke onto the music scene in 2017 with her EP; however, she was unfortunately dropped by her label in 2020—but Roan didn’t let that little speed bump slow her down. She went on to release her first studio album, The Rise and Fall of a Midwest Princess, in 2023. The album took the world by storm a year later, with the artist all but claiming the summer of 2024 as her own with mega-hit songs like “Good Luck, Babe,” “Pink Pony Club” and “Hot to Go!”

From there, Roan regularly went viral online thanks to her incredible festival performances, high-energy concerts and authentic attitude. She also earned eight nominations at the 2025 Grammy Awards, taking home the Best New Artist trophy. Still, aside from her fabulously fun sound and wonderfully wild stage presence, there’s another thing Roan is known for: her unforgettable fashions.

As the artist has noted herself, Roan’s persona has been predominantly influenced by drag culture, with camp aesthetics and shocking silhouettes making up the majority of her marvelously memorable wardrobe. From her outstanding onstage outfits to her headline-making red carpet moments, Roan has truly become one-of-one in the fashion space over the last couple of years.

So with that in mind, we’re taking a look back at just a few of our favorite outfits the artist has worn throughout the years—we guess you could say these picks are H-O-T-T-O-G-O.

Onstage persona

As stated above, Roan’s onstage persona pulls inspiration from iconic drag queen-inspired aesthetics. Her exaggerated makeup is typically paired with plenty of playful pieces, often channeling a specific theme or vibe for the entirety of her show, depending on the city she’s playing in or the festival she’s performing at.

Going green in New York City

Channeling luchador vibes at Lollapalooza

Keeping it cool in latex at Coachella

Mixing reds and blues in Berlin

Casually rocking some camo in London

Giving fringe the spotlight in Chicago

Making medieval style modern at the MTV VMAs

Featuring florals for a duet with Olivia Rodrigo

Cover girl cool

Roan’s styling for magazine features runs the gamut. While some outlets spotlight her onstage persona, others opt for a more natural look. No matter the aesthetic, Roan always brings her signature cool confidence and sensational sensibilities to the forefront, giving fans plenty of reasons to collect every feature.

Perfectly styled in leather for Perfect

Looking “wild, whimsical and wonderful” for W Magazine

Rocking a radiant eye for Rolling Stone

Piling her hair high for Paper Magazine

Giving a masterclass in mixing patterns for NME

Red carpet rock n’ roll

While all of Roan’s ensembles are memorable and headline-worthy in their own right, there’s no denying that her red carpet looks are where she tends to go all-out. Channeling her onstage style, Roan often dresses with a theme in mind, combining opulent pieces with unique accessories and breathtaking makeup for one-of-a-kind, camp-classic looks that are as memorable as they are magnificent.

Modeling a magical headpiece at the Rock & Roll Hall of Fame

Rocking 1980s rock star vibes at the Met Gala

Foreshadowing her onstage theme at the MTV VMAs

Bringing bright colors to the forefront for the Grammy Awards

Taking statement dressing to the next level at the Fashion Awards

Looking ahead: What’s next for Roan?

As we noted at the start of this article, the last two years of Roan’s career have seen her catapulted into the spotlight as not only a rising star in music, but a serious contender in the fashion space. Any red carpet Roan walks is all the better for having her presence, and her looks have no doubt inspired other artists to up the ante.

Following her breakout year in 2024, Roan released two new songs in 2025: “The Giver,” a tongue-in-cheek, country-style tune, and “The Subway,” a beautiful, heartbreaking breakup ballad. The latter was released with a corresponding music video, which saw more of Roan’s creative storytelling skills featured through fashion and beauty.

Looking ahead to 2026, fans will unfortunately have to wait a little longer for a new album, with Roan being candid about the fact that she’d prefer to take her time developing her next work, rather than rushing to put something out.

“It took me five years to write the first one, and it’s probably going to take at least five to write the next. I’m not that type of writer that can pump it out,” Roan told Vogue of her plans back in August. She also added, “I don’t think I make good music whenever I force myself to do anything.”

Still, fans can rest easy knowing that, where there’s a red carpet, they’ll likely be Roan, rocking another out-of-this-world look that will inspire us all to have a little more fun with our wardrobes.

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Published Dec 24, 2025

ALLIE HAYES

Allie Hayes is an experienced pop culture staff writer and editor specializing in movies, TV and celebrity news. Before joining the Sports Illustrated Swimsuit team as a Breaking/Trending News Editor, she worked at several outlets including BuzzFeed, The Daily Dot, and Newsweek. When she’s not writing for work (or writing for fun), you’ll find her curled up on the couch reading yet another romance novel, obsessively watching pro wrestling with her friends, or taking blurry photos of her two adorable cats.