How Chappell Roan’s Stylist Turned Her Into a Swan for ‘The Tonight Show’

Chappell Roan was molting. As Ms. Roan, a pop artist on the rise, walked onstage to appear on “The Tonight Show” last week, raven-black feathers drifted from her minidress onto the stage at 30 Rock. Feathers at least three feet long stuck out from her neckline all the way to Jimmy Fallon’s desk, nearly brushing his coffee mug.

“I was like, Fallon’s going to get his eye poked out,” said Genesis Webb, who had spent the past three months gathering plumage in her capacity as Ms. Roan’s stylist. She outfitted the singer in an eerie black swan dress for the interview segment, and then replaced it with a white swan tutu for the musical performance. There were so many components to worry about — headpiece, fishnets, pheasant feathers to glue to the singer’s face — that Ms. Webb barely slept the night before the taping on Thursday.

But that is the joy, and the challenge, of styling one of the most bombastic dressers of this moment in pop. “She wants to go as big as possible,” Ms. Webb, 26, who lives in Los Angeles, said in an interview this week. “If you’re not pushing something, then why are we doing it at all?”

Ms. Roan has spent the past few months romping across bigger and bigger stages, in outfits that combine outrageous costuming with the kind of artful tackiness honed by drag queens. (The performer, whose real name is Kayleigh Rose Amstutz, has described Chappell Roan as a drag persona of sorts.) Each look seems to one-up the last: She accessorized a hot-pink prom dress with a cigarette butt in her hair for an NPR Tiny Desk Concert in March, and performed at the Governors Ball music festival earlier this month dressed as the Statue of Liberty, her entire body — buttocks included — painted green.

The singer’s fans eat it up, even if Mr. Fallon appeared a bit dumbfounded by the avant-garde, avian look across his desk on Thursday. “We pull from drag, we pull from horror movies, we pull from burlesque, we pull from theater,” Ms. Roan explained to him. “I love looking pretty and scary, or like, pretty and tacky. Or just not pretty.”

That philosophy is shared by Ms. Webb, who said she aimed to make the singer look “glamorous, but also ugly and confusing.” The two met on a shoot for V Magazine last year, where Ms. Webb was assisting Nicola Formichetti, the longtime Lady Gaga collaborator and former designer of Diesel and Mugler. They bonded over a love of vintage clothing and their small-town upbringings — Ms. Roan in Missouri, and Ms. Webb in Oklahoma.

Ms. Webb began conceptualizing the swan look last year after watching the film “The Fisherman’s Daughter.” She showed Ms. Roan a shot of two women in white dresses and swan-shaped hats, and they started coming up with other related reference points, including the ballet “Swan Lake” (specifically the “Barbie” movie version released in 2003) and “The Horn of Plenty,” the feathery Alexander McQueen show in 2009.

Ms. Webb enlisted the designer Gunnar Deatherage to create a white performance dress that recalled an unsettling ballerina. They went back and forth on designs for about three months, with input from Ms. Roan, who requested a shorter tutu. Ms. Webb felt strongly that the pearls on the bodice of the dress should look as if they were spilling out of the singer’s organs.

“It doesn’t look like, ‘Oh, a pretty swan,’” Ms. Webb said. “It looks scary, almost like it could be in a horror film.”

Two days before the taping, Ms. Webb got a black feathered dress with a tighter silhouette and a sculptural bust line from the fall 2024 collection of the brand the Blonds. Together, the two looks conjured the duality played up in the 2010 thriller “Black Swan,” she said: a more demure performance look, and a saltier one for the interview with Mr. Fallon.

“I Googled you today, just to see what popped up,” Mr. Fallon said, in a snippet that has since been circulating on social media.

“Did you not know who I was before?” Ms. Roan responded.

The artist known as Andrew Dahling spent more than two hours on Ms. Roan’s makeup for the appearance, which included pale face powder, pink under-eye shading and eyelashes exaggerated by ghostly, white feathers. “It had to be coming out of her eyes on to her face, like she was an ‘Animorph’ bird,” said Mr. Dahling, who has also done makeup for the nightlife fixture Susanne Bartsch.

He made up Ms. Roan in homage to the drag queen Divine for Kentuckiana Pride in Louisville this month, and painted her body green for Governors Ball. That took more than four hours and two layers of green paint.

“To a normal person, the extremity of it, the pain and the inconvenience of it all would have just been annoying,” he said. Not so for Ms. Roan and her styling team. “Whatever it takes to get the look, we’re into it.”