CNN
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How many modern pop stars adopt makeup from the 15th century? At least one. Musician Chappell Roan, 26, made her long-awaited 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 a camp version of medieval feminist icon Joan of Arc. “If Joan of Arc was a glamour girl,” joked Roan’s makeup artist, Andrew Dahling, who worked on the VMAs vision. Roan — who won Best New Artist — sang her hit “Good Luck, Babe!” in a full chainmail knight’s outfit in front of a flaming castle, her chestnut locks styled in two back-length braids. The sense of historical accuracy in her costume, however, came to an abrupt halt above the neck. Roan’s white-as-a-pebble face was a delicate blush of mauve at the cheeks, and her brows were blocked out in favor of two pencil-thin lines. A theatrical smokey eye, composed of iridescent blue, purple and gold shadow, was blended all the way up to her browbone.

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

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

Roan’s meteoric rise can be attributed, at least in part, to her tireless dedication to transforming into different personas. In the past four months, she’s appeared as an NFL player complete with rhinestone-embellished shoulder pads and “eye black” stripes at Alabama’s Hangout Festival, a latex-clad WWE wrestler at Lollapalooza in Chicago and a sage-green, joint-smoking Lady Liberty at New York’s Governors Ball. (Dahling, who was behind Roan’s green body paint and makeup, said it took her about four hours to complete the look.) Though she’s rarely without her trademark powder-white face — a ghostly base that would make even Queen Elizabeth the envious.

Ahead of her European and UK tour later this month, Roan even released a series of themes and accompanying mood boards with instructions for fans on how to dress for her shows, from mermaids for the Manchester show to camo 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 showcase.” With her makeup, creativity is king, while the conventional, social media-ready glamour that has come to define modern beauty standards often takes a back seat. “It’s not meant to look classically beautiful (like) the Instagram makeup that we see today, which is super blended and perfect,” Dahling said of Roan’s VMAs look. “There’s nothing wrong with that.”

The pop star calls herself a “drag artist” — a term typically reserved for male performers who use makeup to create and embody outrageous, theatrical female personas. Despite being a woman, Roan often paints her face in direct references to famous queens like Divine, the actor, artist and John Waters muse who inspired the look for her Kentucky Pride appearance. Violet Chachki, the season seven winner of the reality competition “RuPaul’s Drag Race,” was also an inspiration for Coachella. “Violet Chachki has that black negative space, smoked out look that she has,” Davy said. “I remember that was on one of the first mood boards that Chappell’s stylist gave me.”

If the concept is confusing to some, it shouldn’t be, Dahling said. “Drag is such an umbrella term, especially now… I think everything is drag,” he told CNN. “Drag could honestly be a guy (who works in the Financial District) putting on a really nice suit and going to the office, (embodying) this version of himself that he’s created.”

“It’s about creating a new face,” Davy said. “You’re blocking in the eyebrows, which means you’re gluing them down, and then you’re putting concealer over them to make them more exaggerated. It’s carving out the cheekbones. It’s making an exaggerated lip shape, contouring the nose. Then it’s a big dramatic eye look. … It’s taking on this character that you’re turning into. … I don’t think it’s gender adaptive.”

Dahling agrees. “There are no rules,” he said. “It’s playful. It doesn’t have to be perfect… it’s very much a DIY feel.” While he maintains that “the messier the better,” Dahling does have one non-negotiable for fans looking to emulate Roan’s look: mastering her now-iconic Venetian white foundation. “No patchiness with the base,” he laughs. “The base has to be right.”