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The Giver of Looks: Chappell Roan’s Most Iconic Fashion Moments

Chappell Roan isn’t just becoming an icon in the music industry—she’s redefining fashion with her bold, drag-inspired style. Here’s a deep dive into some of her most memorable looks.

Illustration by Aimee Coello/Trill

Over the past couple of years, Chappell Roan has transformed from an unknown talent like so many other aspiring artists into a global phenomenon. Her commanding stage presence and queer pop anthems have left her audiences captivated. Chappell’s musical talent has certainly been the catalyst to her rise to fame. However, she has become almost equally well known for her campy drag-inspired fashion looks.

Chappell released her debut album, The Rise and Fall of a Midwest Princess, in September of 2023. While it was not a charting album upon release, 2024 was Chappell’s year. Her songs “Casual” and “Red Wine Supernova” began to take off in March 2024. But it wasn’t until Chappell released “Good Luck, Babe!” in April that she cemented her place in pop music. Then came “The Giver,” a fun, queer country single that dropped earlier this year, proving her versatility and inspiring the very article you’re reading.

Despite not seeing widespread popularity until this past year, Chappell opened for Olivia Rodrigo’s SOUR Tour in 2022 and GUTS Tour in 2024. She also provided backing vocals for both of Olivia’s albums. Coupled with her hugely successful Coachella sets in April 2024, Chappell Roan truly began to appear on people’s radar.

While she is clearly a vocal talent, it was her visual identity that finally propelled Chappell to stardom. She’s been open about her fashion inspirations, often citing drag culture as a guiding source. 

So, let’s celebrate the looks that not only tell stories but are helping to write Chappell’s own. 

Lady Liberty: A Star-Spangled Statement

Chappell’s Statue of Liberty-inspired performance costume is one of her most memorable. Performing at Gov Ball, she took being “Naked in Manhattan” literally when she arrived on stage as Lady Liberty herself. 

Covered head to toe in green, the singer had her audience roaring as she emerged from a giant red apple with a smoking blunt in hand. Complete with green body paint, a spiked crown headpiece, and a breezy skirt, Chappell turned the stage into Ellis Island. The performance was an ode to New York City as well as a political statement about freedom, queerness, and visibility.

With a booming quote from the Statue of Liberty’s inscription—“Give me your tired, your poor, your huddled masses, yearning to breathe free”—Chappell dedicated her performance to promoting trans rights, women’s rights, and freedom for all oppressed people in occupied territories.

Saint or Sinner? Swordplay on the Carpet

When Chappell Roan stepped onto the 2023 MTV VMAs red carpet in a sheer burgundy gown, chainmail gloves, and clutching a gleaming broadsword, the internet collectively lost its mind—not just over the drama of the look, but over what it meant. Was she channeling Joan of Arc, the martyred warrior-saint? Or was this a nod to Julie d’Aubigny, the scandalous 17th-century bisexual opera singer and swordswoman?

The answer might be: both.

The look walks a thrilling line between the sacred and the scandalous. Chappell’s performance that same night only deepened the ambiguity. She performed fully suited in silver armor, commanding the stage like a pop crusader. Was she the martyr or the menace? Whether you see her as Joan or Julie, the message is clear: she’s rewriting the script, sword in hand.

Divine Drag: Referencing Queer Canon

At the 2024 Kentuckiana Pride Festival in Louisville, Chappell Roan captivated the audience with a striking homage to the legendary drag icon, Divine. She graced the stage in a custom-made, form-fitting red gown, complemented by a leopard-print bodysuit peeking through. Her voluminous, teased red curls accentuated the look, coupled with bold makeup inspired by Divine’s signature style. 

Chappell’s choice to emulate Divine was a deliberate nod to queer culture and its trailblazers. The singer captioned her Instagram post, “I like to believe Madame Divine was watching over the performance.” This tribute not only highlighted Chappell’s deep respect for drag artistry but also underscored her dedication to honoring the pioneers who paved the way for contemporary queer performers.

Swan Lake: Chappell’s Gothic Fairytale

In one of her more balletic and haunting looks, Chappell brought “Swan Lake” to late-night television. Offering up two looks for the night, she channeled White Swan Odette and Black Swan Odile.

During the interview portion of the show, Chappell wore a black corset bodysuit complete with dramatic feathered decals. Her matching feather eye makeup and nails had her resembling a fallen ballerina plucked from a gothic fairytale.

For the performance portion of the night, the singer took on the white queen persona, with a matching white feathered dress and sky-high winged headpiece. Her blood-red lips accentuated every aching lyric of “Good Luck, Babe!”

The outfits presented a dramatic visual that echoed the melancholic undertones of her lyrics. It was also a masterclass in contrast: delicate textures, but bold, bruised beauty.

WrestleMania: She’s the Main Event

Nothing says “camp” quite like a shiny wrestling leotard. At Lollapalooza, Chappell threw down in a sparkling pink and blue one-piece. Her accessories, a star-covered belt and matching wrestling mask, drew inspiration from lucha libre attire.

This look was pure character play. She took to the stage not just as a pop star, but as a larger-than-life persona, turning the stage into her own personal wrestling ring and dominating. Her look had her fans ready to rumble during the show-stopping performance.

Metamorphosis: Chappell Spreads Her Wings

Chappell’s butterfly look at Coachella Weekend 2 was all wings, shimmer, and transformation. With glittering winged sleeves and a bodysuit adorned in iridescent textures, Chappell gave us a true metamorphosis. Her ginormous wings were quite a sight as she flounced around on stage, emulating all the grace and beauty of a butterfly.

Chappell attributed her inspiration for the ensemble to Lady Miss Kier, a singer and fashion icon who wore a similar butterfly look for her performance at Wigstock in 1992. Channeling her fashion influences, Chappell brought a unique flair to the outfit, making it her own. 

The butterfly felt very symbolic: this was Coachella, her biggest platform yet, and she was literally showing us how she had evolved. 

Saddle Up: The Midwest Princess Takes on Country

Debuting her newest single “The Giver” on Saturday Night Live, Chappell embraced her Midwest roots for a fun-filled night of country-inspired fashion. Maintaining her campy signature style, she donned a pink and white checkered two-piece set with pale blue bows. Her matching cowboy boots and fringed arm pieces gave the outfit an extra country glam finish.

“I can’t call myself the Midwest Princess and not acknowledge country music, straight up,” Chappell expressed during an interview with Amazon Music. She continued, “It’s not me trying to cross genres…I just think a lesbian country song is really funny.”

Chappell certainly got the job done with this performance, clearly articulating all of her intentions with this newest release. It kept all the fun, pop-based elements we know and love from her while paying homage to her queerness and her country roots.

“Eat Me:” Order Up, She’s Hot to Go

At Coachella’s first weekend, Chappell delivered a performance that melded provocative fashion and a nod to pop culture. She donned a white latex bodysuit emblazoned with “Eat Me.” With her bandmates wearing matching “Eat The Rich” tops, her outfit hints at a subversive, self-aware comment on the music industry’s commodification of rising artists. 

A silver-studded leather harness and matching choker necklace complemented the outfit. The latter was inspired by Drag Race champion Violet Chachki, highlighting Chappell’s deep ties to the drag community. She accessorized with cheetah-print tights, adding a wild flair to the look. 

Her long, crimped red hair and bold makeup—featuring pale foundation and dramatic black winged eyeliner—enhanced the ensemble’s theatricality, mixing elements of drag and ’80s punk glam. This performance underscored Chappell’s commitment to blending humor, cultural references, and a celebration of queer culture in her artistry.

Burlesque Beauty: A Jazz Age Extravaganza

For her Saturday Night Live promo, Chappell transported us to the opulent world of the Jazz Age with an outfit that was nothing short of spectacular. Collaborating with designer Gunnar Deatherage, the design team crafted a look inspired by early 20th-century burlesque performers. 

The intricate design featured dragonfly wings extending from Chappell’s hips. Together with the headpiece, these accessories were adorned with over 1,000 chartreuse crystals. The ensemble took approximately 500 hours to create. It was initially intended for a music festival but was deemed more suitable for a stationary promo to preserve its complexity. This outfit, one of her most underrated in my opinion, showcased Chappell’s flair for theatrical fashion.

Tiny Desk, Big Persona: A Supernova Performance

​In her NPR Tiny Desk Concert, Chappell delivered a performance that was both visually stunning and deeply reflective of her unique artistic persona. She donned a frilly fuchsia dress paired with a red beehive wig. Silver butterflies and cigarette butts adorned the wig, topped with a silver tiara.

This outfit, coupled with her white face makeup, bold blue eyeshadow, and magenta lipstick carefully positioned on her front teeth, all became symbolic of Chappell’s sense of style. Her performance on the web concert series occurred just before her massive rise to fame, so this look took social media by storm. 

The performance exemplified Chappell Roan’s flair for theatricality and her commitment to pushing boundaries. It solidified her status as a distinctive and influential figure in contemporary pop culture.​

More Than Music: Chappell Roan’s Impact on Art and Identity

Chappell Roan doesn’t just wear clothes—she tells stories. Each look is a transformation, a persona, a statement. Her drag-inspired fashion challenges the binaries of beauty, femininity, and performance. In a pop landscape often dominated by minimalism, Chappell proudly goes maximalist, unapologetically queer, and totally theatrical.

Her outfits resonate not just because they’re beautiful, but because they’re brave. For many in the LGBTQIA+ community, especially trans and nonbinary fans, Chappell represents a future where pop stars don’t conform but explode the mold entirely.

In the age of “The Giver,” Chappell Roan is giving us more than music. She’s giving us art, fashion, politics, joy, and—above all—a reason to watch.

Written By

Hi, I'm Cece, a lifestyle writer with a degree in English from Monmouth University. I'm passionate about storytelling, pop culture, and exploring the latest trends in fashion, wellness, books, and everyday life. When I'm not writing, you can find me curating hyper-specific playlists, diving into new books, or exploring my local community in Lancaster, PA.

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