The Complete Transformation Of Chappell Roan

It's been a while since we last witnessed the rise of a true pop star, especially one who encapsulates queer pop with such ease and enthusiasm that they also amass a major mainstream following all on their own. In fact, the last true rise of a superstar who had a huge impact on the music landscape was arguably Lady Gaga, who influenced not only music but also fashion and beauty in big ways. That's all coming to an end now, though, as one singer is experiencing a strikingly similar ascension to Gaga's rise: Chappell Roan.

You may have heard her songs while scrolling on TikTok, or maybe you've seen her iconic outfits from her Tiny Desk Concert or Coachella set. Either way, it's hard to escape the 26-year-old musician, who describes herself as "rhinestone, explosive, innovative, bold, and feminist" (via PopCrave). And honestly, we're not complaining — the music industry was ready for a new queer icon who delivers genius lyrics and a voice we can't get enough of, and here at Glam, we're oh-so ready to explore her campy fashion and makeup. 

Born and raised in Missouri, Chappell Roan, whose legal name is Kayleigh Rose, embarked on a career in music as a teenager. At the time, her style was  bohemian and whimsical with a hint of gothic — all of which can be seen and heard in the song "Die Young," which she originally uploaded to YouTube in 2014. Soon after, she signed a deal with Atlantic Records. "At the very beginning, I was doing a lot of dark synth pop. It was ballady, witchy, and melodramatic. I listened to Lana [Del Rey], Lorde, and Ellie Goulding ...," the singer explained to PopCrave. 

In 2017, Roan admitted that picking her stage name was a tough task. "The picking of the name was the hardest part of this entire thing," the musician told News Leader. "It was the most stressful part." She chose the name in honor of her grandfather, Dennis Chappell, who was battling cancer at the time: "I let him hear rough demos, and I told him I was going to be Chappell in his honor." Meanwhile, Roan comes from his favorite song, "The Strawberry Roan" by Curley Fletcher. Looking back on her teenhood, Roan admitted that she missed out on a lot. "I mourn being a kid because my career took that away from me pretty immediately when I signed. But I also didn't know how to protect myself. I didn't know how to protect my youth and my mental health. And I wasn't diagnosed yet with bipolar. I feel like I did miss out on having friends," she told Vanity Fair of this period in 2023.

By the end of the 2010s, Chappell Roan was known within the industry, but she hadn't reached mainstream fame yet. Her aesthetic remained moody and bohemian, and in 2018, she opened up to Anchr Magazine about the women who influenced her art the most. "Stevie Nicks and Karen Carpenter are my main vocal influences. When I was younger I would try to mimic their voices. Frida Kahlo is my favorite artist. I love the darkness and vulnerability of her paintings," she said, adding, "Lady Gaga and Beyoncé really inspire me with their stage presence. They are both so confident and really own the stage and connect with the crowd so well. I hope to be like them one day."

And while Roan is undoubtedly a unique artist in her own right, we do see a bit of all of the women she mentioned not only in her art but also in her fashion and beauty choices. The star channels Nicks' bohemian and witchy fashion vibes, Carpenter's classic '70s look, Kahlo's love for color and authenticity, Gaga's outrageous fashion and raw emotions, and Beyoncé's unapologetic fierceness. Yet, while all of these women have inspired the young star, it's always been clear that Roan strives to create art as herself: unapologetic, bold, and authentic as can be.

In early 2020, it seemed like Chappell Roan was about to make it big. Unfortunately, the COVID-19 pandemic swooped in, and the musician's rise to fame slowed down. In an interview with I Dream of Vinyl, Roan opened up about her life in lockdown. "I really enjoy being at home and staying bust without the pressure of having to make plans or leave," she said about quarantine life. The star also opened up about her goals for the year: "I would like to start producing my own music, dabble more in movie scoring, finish an album, and learn to live with my anxiety."

While her style wasn't as bold as we know it to be today, there was a noticeable shift in what the musician gravitated toward. The star began rocking her signature cowboy hats and sparkly outfits, slowly becoming more and more comfortable in experimenting with her look. And we'd be remiss not to note that Roan was way ahead of the Westerncore trend that's been everywhere the last couple of years.

In April 2020, Chappell Roan admitted that moving to Los Angeles helped her find her voice as a songwriter. "It was so different from home, where I always had such a hard time being myself and felt like I'd be judged for being different or being creative," she told V Magazine, adding that she felt "[l]ove and acceptance, and from then on I started writing songs as the real me."

Unfortunately, in August that year, the musician's career suffered a setback when Atlantic Records dropped her. This, of course, influenced her mental health, and the star almost gave up on pursuing music. "It was just so bad," she told Teen Vogue in 2023, remembering the period and adding that she also went through a breakup at the same time the label dropped her. "Everything was leading me to tell me that I need to stop. Nothing's working... I was 22 and I was like, what is this anymore? I don't know." Luckily, the star didn't give up, and even though she went through a tough time, she would soon become one of the biggest rising pop stars.

The single "Pink Pony Club," originally released in early 2020, signified a major change for the star. Her sound became more pop, her fashion became more dramatic, and her overall vibe became a lot bolder. "I wanted to wear weird, fun clothes, and I felt like I couldn't do that with Die Young. It just felt too dark, so I purposely was like, 'I have to change, because this is not sustainable'," Chappell Roan admitted to Headliner. "I wanted to push myself – I wanted to be bold and say things that might be a little edgy." The single, which was inspired by the iconic LGBTQ+ bar The Abbey in West Hollywood, became a huge hit among her fans by the end of 2020.

The star also explained to Headliner that her shift toward a louder and more colorful aesthetic was an authentic choice: "I needed to be myself and I wanted to feel theatrical; I wanted it to feel like a show for people. That's what I feel like Pink Pony Club is doing and what my other music that will come out will do as well." And it's exactly the over-the-top drama and theatricality that eventually led the star to catch the eyes of a much wider audience.

By early 2022, Chappell Roan had gone viral on TikTok, and she now had an opportunity to reach a global audience. "I go so back and forth with TikTok," she told Billboard that year. "I gained a lot of speed at the beginning of the year with TikTok because I wasn't busy; I had time to post twice a day, go live once a day, repeat. It doesn't work when you're busy." Around this time, she was also chosen as an opening act for Olivia Rodrigo's Sour Tour.

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Though TikTok helped the musician share her music, Roan has experienced a love-hate relationship with it. "TikTok was just a way to display my personality and the inner workings, but I feel like it was hell most of the time trying to get it together as an independent artist and also having a part-time job," she admitted to People the next year. "The app breeds mental illness. When I was really, really sick and I was posting twice a day and going live every day, it rewards that type of behavior. I had to really figure out what was right for me, and I'm still figuring that out." Roan, who was diagnosed with bipolar II disorder, has always been open about her mental health with her fans.

The more self-acceptance the star found, the braver her fashion and beauty choices became, and in the first half of 2022, we got to see her post plenty of funky and colorful makeup looks on Instagram. Of course, this was just the beginning of the star's experimentation with makeup and all it can offer.

In August 2022, Chappell Roan released "Femininomenon," a funky anthem that gave us a reason to head to the clubs, and a couple of months later, she admitted to Billboard that she finally saw a future for her music. "Last year I was working at a doughnut shop, so I'm doing great now," she said. "It's validating ... but also not surprising to me. Like, yeah, I've been working my ass off for seven years! It's about time!"

Roan also admitted that finding her way in the industry had a lot to do with finding herself. "Once I let go of trying to be this very well-managed, put-together pop girl, it felt like everything just fell into place," she told the magazine. "I leaned into the fact that my looks were tacky ... I leaned into my queerness for the first time. When I did that, the songs got easier to write, the shows got easier to design, and my aesthetic was finally there." 

When Roan embraced her truth, she created a space for others to do the same. "If I can create a space where people can afford to come into a mostly queer space... then that is great," she added. And whether she was fully aware of it or not, Roan's self-acceptance was already making her a major role model for young queer people across the globe. One thing we didn't think was possible, though, was for her makeup looks to become even wilder, but she proved us wrong on Instagram with looks that screamed "Chappell Roan" in the best way. Anyone who adores glitter is after our hearts.

In early 2023, Chappell Roan signed a record deal with Island Records, but it was clear that Roan wasn't going to be put into any pop-princess mold. In fact, the musician was clear about using her platform to speak her experiences and beliefs, and fans adored her for it.

In an interview with Teen Vogue, she opened up about her queerness and how she handled it as a teen. "I was like, girls are so much prettier," she explained. "Girls are nicer. I like hanging out with girls more. That was in the back of my head for all of high school. I think I like girls." Then, for Daily Trojan, she talked about her mental health, explaining how she keeps herself a priority by going to therapy. "I was diagnosed with bipolar II disorder when I was 22. Medication really, really helped me. Taking care of myself really helped me," she said. "Honestly, being single really helped me. I think we just really don't take care of ourselves, sometimes, when we are dating someone."

The star has also been a huge supporter of trans rights, using her fame to speak out about the difficulties this community faces. "Let's redistribute our fund to the trans community right now. Let's make sure our trans community is okay on rent. Let's have each other's backs right now. Let's be safe and watch out for each other," she urged in her interview with Teen Vogue. Between speaking candidly about her queerness and mental health and raising awareness about issues faced by members of the LGBTQ+ community, Roan has positioned herself as a young star who isn't afraid to speak up.

With the release of her debut album "The Rise and Fall of a Midwest Princess," Chappell Roan's status as a new pop star on the horizon was established. In an interview with Vanity Fair, Chappell admitted that even though her stage persona is as dramatic as can be, she actually likes to keep to herself. "I am very introverted. I love being alone," she said. "I love playing video games by myself. My favorite thing to do is get really high and play Fortnite or Mario," she added, noting that she avoids wearing heavy and dramatic makeup unless she's on stage.

The pop star admitted that her makeup and fashion choices are also related to her therapy sessions, as they help her heal. "I accepted this branding–I hate to call it branding–by doing inner child work with my therapist. That's how I got to this conclusion that I needed to be a tacky pop star," she said. "I had to let go of the adult in me that thought, 'oh, I need to be so sophisticated and serious and so good at everything or else I'm not good enough'." And by accepting the choices her inner child would make, Roan managed to become a fashion icon that is both incredibly extravagant and somehow incredibly genuine. As seen in an Instagram post to celebrate the album's release, she's even shaved her eyebrows for her craft. That's dedication!

Though 2023 was a major year for Chappell Roan, she didn't become a global pop star until 2024. During her anything-but-basic performance at Coachella, she told the audience, "I'm your favorite artist's favorite artist," referencing drag queen Sasha Colby's famous saying,"I'm your favorite drag queen's favorite drag queen." At the time of writing, "I'm your favorite artist's favorite artist" now appears as the "Did you mean" option when one searches Roan's name on Google.

The star has continued advocating for the queer community, acknowledging that the community is where most of her fans come from. "The queer community is my main fanbase, so my responsibility is to pay it forward by donating a portion of ticket sales and sales in general [to LGBTQ+ charities] and show up at Pride events," she told NME this February, adding that she's "here to give back all the energy that the queer community has given [her]."

Fashion-wise, the star began rocking even more intricate and eye-catching looks, even rocking a prosthetic pig snout to a 2024 Grammy Awards after-party. During an interview on the "Q with Tom Power" podcast, the musician revealed that her looks are reminiscent of drag. "A drag queen opened for me in London, named Crayola. She was like, 'Oh, you are a drag queen'," Roan revealed. "And I was like, that was the first time I'd ever been told that. I was just getting ready, and like, my makeup wasn't done yet, and I was like, 'Oh you know I'm like you. I need to get my makeup and my clothes on and kind of transform.' And she was like, 'Honey, you are a drag queen'."

In June 2024, Chappell Roan made a major statement by declining a White House invitation to perform for Pride. "In response to the White House, who asked me to perform for Pride, we want liberty, justice, and freedom for all," she said during her Governors Ball performance. "When you do that, that's when I'll come." What made the moment even more iconic was the fact that she was dressed as the Statue of Liberty — green body paint included.

Also in June, the musician appeared on "The Tonight Show Starring Jimmy Fallon" in a black swan look (she changed into a white swan look for her performance of "Good Luck, Babe!"). During her interview, Roan told Fallon that she and her stylist, Genesis Webb, take inspiration from a variety of things. "We pull from drag. We pull from horror movies. We pull from burlesque. We pull from theater," she admitted, explaining her tendency to wear over-the-top and campy fashion. "I love looking pretty and scary or like pretty and tacky... Or just not pretty. I love that, too," she added. Ultimately, with redoubtable musical talent and a captivating stage presence, Roan is becoming a once-in-a-generation artist, and we can't wait to see where her sound and her fashion go next.