CNN
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How many modern pop stars take their makeup inspiration from the 15th century? At least one. 26-year-old musician Chappell Roan made her highly anticipated VMAs debut last night, hitting the red carpet in a sheer Y/Project gown, thigh-high knight boots, and a face painted like a ghostly Renaissance woman.

Later in her performance, Roan switched centuries — transforming into an emotive version of medieval feminist icon Joan of Arc. “If Joan of Arc was a glamour girl,” quipped Roan’s makeup artist Andrew Dahling, who helped create the VMA vision. Roan — who won best new artist — sang her chart-topping hit “Good Luck, Babe!” in a chainmail knight costume in front of a burning castle, her auburn locks braided into two back-length pigtails. The sense of historical accuracy of her costume ended abruptly above her neck, however. Roan’s chalky white face was painted soft mauve on the cheeks, and her brows were drawn in with two pencil-thin lines. She had theatrical smoky eyes of iridescent blue, purple and gold eyeshadow blended all the way to her brow bone.

Dahling was inspired by Pat McGrath’s work as a makeup artist for Dior in the 2000s. “It’s very romantic,” he told CNN in a video call from New York in the days before the awards ceremony. “But kind of darkly romantic… Very strong on the eyes, very luminous skin, very ethereal… (Every look is) very much in that medieval Renaissance realm.”

For Roan’s red carpet look, Dahling went for a lighter touch. The singer’s chalky complexion was soft and blurred, while her eyes were magnified by a rim of white eyeliner and finished with a delicate touch of gold. Dahling wanted to evoke the plump, peachy faces of women immortalized in oil paintings from the Renaissance and Baroque periods. “I love being inspired by artists and painters,” he said. “Because I feel like their perspective captures something that’s a little different than what a makeup artist would do.”

Roan’s meteoric rise is due at least in part to her tireless dedication to transforming herself into different characters. In the past four months, she’s appeared as an NFL player with rhinestone-studded shoulder pads and “eye black” stripes at the Hangout Festival in Alabama, a WWE wrestler in latex at Lollapalooza in Chicago and a sage-green, joint-smoking Statue of Liberty at the Governors Ball in New York. (Dahling, who was behind Roan’s green body paint and makeup, said the look took about four hours.) However, she’s almost never without her trademark powder-white face – a ghostly foundation that would make even Queen Elizabeth envious.

Ahead of the European and UK legs of her tour later this month, Roan even posted a series of themes and accompanying mood boards instructing her fans on how to dress for her shows: from mermaids at the Manchester show to camouflage for Glasgow and London. “She has such a strong vision,” Dahling said. “And this larger-than-life, superstar version of herself that she wants to show.” Her makeup is all about creativity, while the conventional, social media-ready glamour that defines modern beauty standards often takes a back seat. “It’s not meant to look classically beautiful (like) the Instagram makeup we see today, which is super blended and perfect,” Dahling said of Roan’s VMA vision. “Quite the opposite.”

The pop star calls herself a “drag artist” – a term usually reserved for male performers who use makeup to create and embody flamboyant, theatrical female characters. Although Roan is a woman, she often paints her face with direct references to famous queens like Divine, the actress, performer and muse of John Waters who inspired her look at Kentucky Pride. Violet Chachki, the winner of season seven of the reality competition “RuPaul’s Drag Race,” was also an inspiration for Coachella. “Violet Chachki has this black, negative space, this smoky look,” Davy said. “I remember that was on one of the first mood boards I got from Chappell’s stylist.”

If the concept is confusing to some, it shouldn’t be, Dahling said. “Drag is such a catch-all term, especially now … I think everything is drag,” he told CNN. “Drag could honestly be a guy (working in the financial district) putting on a really nice tuxedo and walking into the office and (embodying) this version of himself that he’s created.”

“It’s about creating a new face,” said Davy. “You cover up the brows, which means you stick them in place and then put concealer over them to give them a more exaggerated shape. It’s about bringing out the cheekbones. It’s about creating an exaggerated lip shape and contouring the nose. Then you do a big, dramatic eye look… It’s about embracing this character that you’re slipping into… I don’t think it’s gender specific.”

Dahling agrees. “There are no rules,” he says. “It’s playful. It doesn’t have to be perfect… it’s more of a DIY feel.” Although he insists that “the messier the better,” Dahling has one must-have rule for any fans hoping to recreate Roan’s look: mastering her now-iconic Venetian white foundation. “No staining on the base,” he laughs. “The base has to be good.”