How Chappell Roan’s Stylist Turned Her Into a Creepy Swan (Twice)

Genesis Webb helps the rising pop star put together drag-inspired looks that are “glamorous, but also ugly and confusing.”

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.”