Andra Day

Andra Day Enters a New Season

From celebrated singer to Oscar-nominated actress (in her first-ever role), Andra Day has translated her unparalleled soulfulness into stardom.

Zoom be damned, as Andra Day sits comfortably on a hotel couch in Los Angeles, resplendent in a poppy red floral kimono over a shimmering, emerald green silk camisole. Hair a gorgeous tangle on top of her head, eyes like almonds, and large, thin hoops framing her high, smooth cheekbones, Day exudes immediate presence. It's that flicker of bright green, though, that somehow speaks the loudest.

"Green is always with me," says Day. The singer-songwriter-turned-award-winning actress speaks often and openly about her devout relationship with God, and a few years back, she says, she was inspired to highlight in green marker everything in the Bible that had to do with women. Recently Day went back and read over just those passages and discovered something that has stuck with her: "They were messages of leadership, teaching, revelation, and power. Every ministry in the Bible was actually revealed through a woman. That was such an intentionally beautiful thing that I learned."

Day's own path to artistic power began in San Diego, where she started singing in the church choir as a young girl and then later attended the School of Creative and Performing Arts. She knew from the get-go that she wanted to be onstage. "I never had a Plan B," she says. "Tunnel vision, always." That meant no venue was ever too small, and her side hustles were never too offbeat — for a few years in her early 20s, she worked the party circuit and prided herself on her Minnie Mouse impression.

In 2010, fashion designer Kai Millard Morris was in the audience outside of a strip mall in Los Angeles where Day was performing. A moment of ministry ensued. Morris told her then-husband, Stevie Wonder, about Day, and Wonder was impressed enough to connect Day with producer Adrian Gurvitz, who helped launch her music career. The deeply soulful R&B singer can now lay claim to two albums, several EPs, and a pair of Grammy nominations, including for the song "Rise Up," which also became an unofficial anthem for the Black Lives Matter movement in 2017. The social impact of "Rise Up" helped to provide Day with a holistic view of what success means to her. It turns out this was a useful barometer considering that an amped-up kind of stardom was right around the corner.

Andra Day
Versace dress. Wrapped by Nellz headwrap. Hirotaka earrings. Cartier High Jewelry ring, watch, and bracelet. Calzedonia socks. G.H. Bass & Co loafers. Chrisean Rose

This is my second time interviewing Day in recent months. Last fall, I spoke to her for Billie Was a Black Woman, an original Audible podcast I created in partnership with The United States vs. Billie Holiday, the Lee Daniels biopic streaming now on Hulu, and a star-turning vehicle for Day. In the film, Day gives a truly magnificent, gutting début performance, which earned her a well-deserved Oscar nomination in March and a Golden Globe for best actress in a drama in February. Needless to say, the response to her portrayal of Holiday has been overwhelmingly positive, gushing, and constant.

"I can't even process it," Day says, smiling and with a sense of guilelessness that might not ring true on somebody else who has suddenly found herself at the center of a maelstrom of media attention — most of it bursting with expectation. "It just feels like a different world, like a different planet. I still feel like a traveler," she continues. "Kind of a nomadic person in this place. It's just crazy. I'm so grateful."

Andra Day
Hermès scarf. Mateo earrings and rings. Chrisean Rose

Day's version of Holiday is a deeply loving portrayal, a spiritual avatar, illuminating and sensual, rough and rich. Day gives over every last fiber of her being to become Holiday, so it's no surprise that leaving the performance behind has been difficult. In other interviews, Day described the feeling of letting go of her as an "exorcism" or "a divorce." Now, she says, she's in a different place entirely.

"It's a little scary," Day tells me. "Because you're on a precipice a little bit, and you're going, 'OK, who am I? And who am I supposed to be? How am I supposed to be in this season?' "

Andra Day
La DoubleJ dress. Wrapped by Nellz headwrap. Aur Jewelry earrings. Cartier High Jewelry ring (ring finger). Chanel Fine Jewelry ring. M2Malletier loafers. Beauty Beat: A foolproof way to jazz up your eyes is with a chic accent color. Reach for a playful palette such as Chanel Les 4 Ombres in Blurry Green. Chrisean Rose

Day mentions seasons a lot — not the four seasons we observe on the calendar, but rather those distinct periods of time in our personal lives that feel set and preordained, while also wholly out of our control. And whomever Day is meant to be in her current season, she's inarguably knocking it out of the park, certainly in terms of her own clarity and selfhood. Among other things, this time has allowed Day to indulge in her love of fashion. Subsequently, and not surprisingly, there has been a heightened fixation on her image and, of course, her lewks. She's being dressed and courted by fashion houses like Chanel and Prada, and she has consistently dazzled at every awards show and photo op.

"Listen, it's so fun," she says, delighted by the fairy-tale aspect of it. "And it's even more fun now — there's this element of, like, sensuousness. To me, that describes Billie better." Day, who lost 40 pounds for the role, explains that she went into the film being very intentional about keeping the focus of her performance as Holiday on the music, and not on the ways in which she was objectified or hypersexualized in the male-dominated world of jazz music during the 1930s, '40s, and '50s. It was a choice that coincided with Day's little-known internal struggle at the time, in perhaps a darker season.

Andra Day
Dior bralette. Cee Cee’s Closet NYC headwrap. Almasika earrings. Chrisean Rose

"I didn't want any element of sexualization. I had come out of something in my own life — dealing with porn addiction, sex addiction," she says, like we're just a couple girlfriends chatting about everyday weaves and woes. "I'm being very, very candid with you because I'm not the only one. But I knew I wanted all of that very much gone."

Living with Holiday for such an intense stretch of time seems to have gifted Day the opportunity to consider different ways of being and thinking, particularly around the ideas of beauty and sexuality. "I feel now, after playing Billie, that I'm honoring her, and the strength that is femininity. I'm definitely in a healthier place to enjoy that because I'm outside of the addiction, if you will. So, yeah, it's been really fun, because it's been very new for me."

Day's willingness to be so open, steered by her vulnerability and compassion for herself, speaks so resolutely to who she is.

Andra Day
Stella Jean dress. Jennifer Fisher earrings. Cartier High Jewelry ring (middle finger). Chanel Fine Jewelry ring. G.H. Bass & Co loafers. Chrisean Rose

"I've had people ask me, 'Do you feel prettier now that you've lost weight?' I was like, 'Hell, no! I liked being juicy! I was cool,' " she says, laughing. "But I do like the way [the weight loss] feels on my body, I like the way it feels on my joints. You do notice a difference. Besides, to me, there is no such thing as a classic beauty. Beauty takes on so many different forms, in different times and depending on the nation. It's just about being confident, loving yourself, and understanding your value."

Still, in an industry and a culture where understanding your value as a woman, especially as a Black woman, comes with all manner of caveats, does Day herself feel beautiful? "I definitely do. And it has to do with Billie. It was almost like she said, 'Sis, we're going to have to close this, because I have to survive.' She opened me up to valuing myself in a way that I hadn't fully before."

Andra Day
Salvatore Ferragamo overshirt and shorts. Chanel Fine Jewelry earrings and rings. Cee Cee’s Closet NYC headscarf used as a scarf. Chrisean Rose

You know who else values Andra Day? Ms. Regina King. Because even if Day feels like a visitor in a different world, there's one demographic in that world (and really, in most worlds) that is very happy to see her and welcome her into the fold, and that is Black women.

It's already the stuff of legend — the viral video in which King surprises Day by crashing her on-camera interview with Access Hollywood after winning the Golden Globe. King's thrill in pulling off the surprise is as glorious and winning as Day's genuine shock. "I didn't even know she was in the hotel," Day recalls. "I was so grateful for how excited she was, and how personal it was to her. But I was also just shocked as a fan. I was like, 'That is Regina Fucking King!' " After her shock wore off, though, it just became a portrait of Black sisterhood, the lift, the legacy, and the high-knee hops. "When I watched that video back, I said, 'Oh, so Regina has real hops!' "

Andra Day
Gucci jacket, vest, shirt, pants, and loafers. Headscarf, stylist’s own. Beauty Beat: Try a terra-cotta neutral like Giorgio Armani Beauty Lip Maestro Liquid Lipstick in 102 ($38) if you’re looking for a hydrating texture with a velvety-matte finish. Chrisean Rose

Day says she also received flowers that night from, among other Black women, Viola Davis and Naomi Campbell, making the experience for her that much bigger and more meaningful, both an augur and an affirmation. "This is just a season for beautiful Black girl love and unity. And it's amazing."

And that love is all around her. Scripts are pouring in (though there are maybe a handful that have truly grabbed her attention). She's staying grounded thanks to her faith and her family — Day's mother and two cousins live with her, the younger of whom she cares for as if she were her own daughter — and bigger developments are in sight too, including a top-secret project that Day plans to co-produce and co-direct.

As we wind down our conversation, it occurs to me that Day actually knows exactly who she's supposed to be in this particular season she's in — one of purpose and growth, beauty and complexity, and the fierce agency of a Black woman who has arrived. "Somebody was trying to tell me the other day, 'Just make sure you don't get typecast, because you don't want to always be playing the powerful Black woman.' I was like, 'Yeah, I do. I also am one.' "

Lead Image: Collina Strada bodysuit, socks, and shoes. Wrapped by Nellz headwrap. Erdem brooch. Chanel Fine Jewelry ring (left hand). Cartier High Jewelry ring.

Photography by Chrisean Rose. Styling by Julia von Boehm. Sitting editors: Katie Bofshever/A-Frame Agency and Raz Martinez. Hair by Tony Medina. Makeup by Porsche Cooper. Manicure by Jolene Brodeur/The Wall Group. Set design by Daniel Horowitz/Jones Management. Production by Kelsey Stevens Productions.

For more stories like this, pick up the June 2021 issue of InStyle, available on newsstands, on Amazon, and for digital download May 21st.

Related Articles