Behind the Scenes: Every Dazzling Detail From Andra Day’s April Beauty Cover

If you’ve watched The United States vs. Billie Holiday, it’s easy to laser in on the retro influence—stylistically, musically, and aesthetically—Holiday has had on our April cover star, Andra Day. For our first-ever beauty cover, the singer provides an intimate glimpse into her longtime love for Holiday (the jazz icon has been a source of inspiration, Day says, since she was a preteen), but Day is also quick to point out her admiration of other “fierce, strong” women from decades’ past—Pearl Bailey, Diana Ross, and Dorothy Dandridge, to name just a few. A self-proclaimed “vintage little squirrel,” Day’s style and beauty MO have always skewed toward Old Hollywood glamour. She tells me two of her favorite red carpet beauty moments to date have involved dramatic beehive hairstyles, and her love for history has even informed her at-home beauty rituals. For instance, her trade secret for baby-soft skin—donkey’s milk—is a ritual she adopted after reading up on Cleopatra’s ancient Egyptian beauty dogma.

Of course, not all of Day’s beauty essentials are derived from what she laughingly calls “an ass’s ass.” Dreamy pots of La Mer hold a special place in Day’s heart, and for makeup, it’s all about the Chanel lip and brow, plus a handful of various discontinued products from names like Givenchy and Marc Jacobs. Gentle daily exfoliation is nonnegotiable for Day, and certain ingredients like turmeric, saffron, shea butter, sea buckthorn, and coconut oil make regular appearances in her daily skin and hair routines.

Inspired by Day’s versatility, all three of her stunning April cover looks tease influence from a blend of beauty’s best eras. There are the Ross- and Donna Summer–inspired curls punctuated by T Label gloves and a figure-skimming Aliétte dress. There are the ’60s-inspired lashes complemented by vinyl pieces from Ellery and a “snatched” ponytail hairstylist Tony Medina titles “Don’t Play.” Last but not least, there’s the crystal-emblazoned finale that evokes slinky hints of the roaring twenties—complete with a smoky “Femme Fantastica” eye shadow aesthetic, courtesy of makeup artist Porsche Cooper, and an Area headpiece and dress. Because each look deserves its own moment in the spotlight, we went behind the scenes to chat with Day’s longtime glam team to get the inside scoop on the creation of each of our cover star’s beauty moments. Keep scrolling to learn how Medina and Cooper brought each look to life.

“This first hairstyle I did on Andra for the shoot is voluminous and free,” Medina, who has worked with the artist for almost eight years, explains right off the bat. It’s reminiscent of the Studio 54 curls Ross and Jerry Hall had, so I would call this style “Disco Bunny.” If you’re looking to try out a similar look at home, you’ll want a few of Medina’s staples within arm’s reach—a strong-hold hair spray and a high-quality heat protectant. “Everyone needs a great hair spray in their life, especially to ensure longevity in a style, and a great heat protectant is important for protecting your hair. Use one as often as possible,” he instructs.

With an emphasis on amply hydrated skin and a bold lip, Cooper dubs look number one “The Enchantress.” “How the skin is moisturized and prepped before the makeup application is directly related to how well it will endure as the day goes on,” Cooper confirms. “I always take the proper time to really work my wardrobe of skincare products—all La Mer—into Andra’s skin. I never hurry the skin-prep process, and I’m fanatical about facial mists, especially in the age of mask-wearing. I’m diligent about reapplying La Mer’s The Mist ($85) to ensure the skin stays hydrated and revitalized.” Cooper’s shoot-day ensemble also consisted of other moisturizing staples from La Mer, including The Treatment Lotion ($165), The Eye Balm Intense ($235), The Regenerating Serum ($375), The Moisturizing Soft Cream ($345), The Lip Balm ($70), and The Renewal Body Oil Balm ($200), to keep Day’s skin looking effervescent from head to toe.

For the second look, Medina transformed Day’s ’70s-era curls into a lengthy, textured ponytail “snatched tight.” “I’d call this style ‘Don’t Play’ because girls with ponytails like that do not play,” he shares. As for the makeup, Cooper gave Day a Siren-inspired makeup vibe complete with brow-sweeping lashes and artfully applied foundation, concealer, and bronzer for a lifted, ultra-sculpted effect. Cooper, who has also been at Day’s side for a full eight years, describes the artist as “a creative visionary who is willing to push boundaries.” Understandably, she says that approach to beauty makes each and every collaboration extremely fun.

To try a similar look yourself, do like Cooper and opt for high-quality staples from Chanel to create your base: Les Beiges Healthy Glow Foundation ($60) applied with Les Pinceaux de Chanel 2-in-1 Foundation Brush ($50) and Le Correcteur de Chanel Longwear Concealer ($43) applied with Les Pinceaux de Chanel Retractable Dual-Ended Concealer Brush ($42). To add a warm, lived-in flush, finish with a cult favorite from Chanel: Les Beiges Healthy Glow Bronzing Cream ($50) applied with the same brush used for the foundation.

To shine a spotlight on Day’s third look—which was complete with dazzling crystal accents; her smoky, shimmer-laden lids; a glossy pout; and an Area headpiece and dress—both Medina and Cooper kept things classic. “We pulled the hair back into a sleek bun. I’d call this ‘La Reina’ because it reminds me of the legendary singer Selena Quintanilla-Pérez,” Medina says. To keep Day’s skin looking ethereal with a natural, lit-from-within radiance, Cooper stuck to subtle yet strategic makeup staples: Chanel’s Perles de Lumière Illuminating Blush Powder ($70) and the beloved Baume Essentiel Multi-Use Glow Stick in Golden Light ($45), both skillfully blended atop the high points of Day’s cheekbones.

Craving more behind-the-scenes beauty magic? Be sure to check out the dreamy, cosmic vibes from our March cover shoot starring Phoebe Bridgers.