Grammy-Winning Bassist Esperanza Spalding Is Back Onstage With a New Album — And Her Own Special Kind of Style

In a sun-streaked photo studio on West 28th Street, Esperanza Spalding is perched on a large, swiveling makeup chair, dressed in an oversize printed dress she’d plucked from a rack of clothes set up for today’s shoot. We’re chatting as several people tease her hair into Medusa-like twists when she spins around to face me with mock seriousness. “Justin and I? There’s no bad blood. We actually went on a date recently.” I pause, unsure if I’ve heard her correctly. “I’m fucking joking!” She laughs, giving me a merry shove. “But wouldn’t that make a great story?”

It has been five years since the now 31-year-old bassist, singer, and composer won a Grammy for Best New Artist, beating Justin Bieber and, in the process, enraging his loyal fans. A venomous backlash ensued, with thwarted Beliebers venting their disappointment on Spalding’s Wikipedia page (among other things, infamously writing, “WHO THE HECK ARE YOU ANYWAY?”). This didn’t faze Spalding, who says the best thing about winning the Grammy was that it made her big brother cry. “That was the biggest achievement of all, because he’s so serious,” she says. Now, after a three-year hiatus, the Portland, Oregon, native has released her fifth album, Emily’s D+Evolution. Rolling Stone called it “potent” and “seductive,” Pitchfork deemed it “noisily complex” but “gorgeously so,” and the New York Times‘ latest review labeled her “ingenuous and unbound.” If there were ever any doubt about her status as a force in contemporary jazz and soul, they’re pretty well gone now.

Spalding, who currently lives in Brooklyn’s Prospect Heights, is frank about her exit from the music industry in 2013 after winning two more Grammys for her album Radio Music Society. “My whole team got a little overwhelmed by possibilities that were coming in. I felt like I had to manage too many things beyond the realm of my craft and, at 27, I wasn’t prepared for it.” Business and logistics, she says, left little time for musical play. “I decided I was going to stop everything and build it back up from square one, with the basics, which is creating.”

Emily’s D+Evolution, co-produced by Tony Visconti and written in the voice of Spalding’s playful alter ego, Emily (her middle name), evinces this need to start over. In what music critic Nate Chinen called a “syncopated yawp of defiance,” Spalding’s sound is even markedly different, her trademark chamber jazz morphing into a rock/funk hybrid steeped in “mid-1970s r&b, prog-rock, and fusion,” as Chinen explains in his review for the Times. On the album’s first track, “Good Lava,” Spalding offers, “See this pretty girl, watch this pretty girl flow,” a wink to the album’s title and a comment about growth, albeit with a barely passing grade. She parses her own lyrics for me: “Emily’s saying to all the people stuck in paralysis by analysis, ‘You see me, right? OK, now watch this, watch what you can be, too, because it’s not that hard.’ ”

Spalding describes the album, released on March 4, as a state of mind to be channeled in difficult situations. Recalling her own spiral into “paralysis by analysis,” she recounts a time she was on her way to meet a director but had talked herself out of going. “I was so afraid they wouldn’t like me, and I didn’t want to deal with that letdown, so I was going through this whole rationalization of why I shouldn’t go. And all of a sudden I heard this [voice say], ‘You know what? Fuck the fear, live your life! Why would you not go, just for some bullshit fear?’ ” That night, Spalding got home and wrote “Funk the Fear,” a reminder to the rest of the world not to play it safe.

Since the release of her debut album, Junjo, in 2006, Spalding has become a pro at funking her own fear, performing for President Obama twice at the White House and once at the Nobel Peace Prize ceremony, singing alongside the Southern California Children’s Chorus at the 84th Academy Awards, headlining sold-out shows across North America and Europe, opening for Prince (who tweeted Emily’s D+Evolution as his pick for album of the week during this cover shoot), and starring in a Banana Republic advertising campaign.

But that doesn’t mean Spalding has it all figured out. Insubordinate and aggressively independent by nature, she admits it can be “uncomfortable” to navigate show business, and her return to the spotlight, as her “authentic” self. “I always feel pretty exposed because I don’t really have a sound or look, or a cultural reference bag that fits into the common vernacular of what people connect over,” she explains, adding that she often feels ill-equipped to communicate with people she meets at events, award shows, dinners, or “anywhere else” she’s required to perform.

“Generally, when I walk into a space where people don’t really know who I am or what I do, or don’t particularly care, they probably think I’m pretty and here based on some reason that has to do with being pretty,” she says. Indeed, everyone from the New Yorker, which commented on her “serenely beautiful face” in 2010, to this newspaper, which took note of her “gamine” figure in a review last year, has shamelessly remarked on her looks. Perhaps this focus on her “doe-eyed” face, as vogue.com described her last month, explains why Spalding feels awkward in new spaces. “I’m very conscious of that feeling — being on the edge or outside of the club. Not knowing the jargon. It’s uncomfortable.”

I ask her if this discomfort could be an effective tool, a way to easily spot who is (and isn’t) worth her time. Spalding shakes her head, explaining how the business of music can overcomplicate the simplest of interactions. “You’re sitting across from this guy who you know doesn’t give a fuck about you, but he’s acting like he does, so you’re supposed to act like you don’t know he doesn’t really care so he can give you an advance so you can go and do your art. And you’re sitting there like, ‘This is insane, we’re all just lying in each other’s faces over some money.’ ” She laughs before issuing a caveat: “To be fair, though, for every twenty of those people, there is someone who is able to find the graceful balance between business solvency and the artistic ethic. I don’t want to act like everyone’s a complete asshole, because it’s really brave of the ones who take a risk.”

Spalding may not know “the game or the play,” as she puts it, but she does know music, which puts her in a unique position to pull rank when an artistic decision doesn’t sit right. After earning a full scholarship to the Northwest Academy, a private arts high school in downtown Portland, where she played several instruments — the piano, clarinet, guitar, violin, oboe, and, eventually, bass — Spalding joined the pop band Noise for Pretend, first as a bassist and then as lead vocalist. (The band released its only full-length, Happy You Near, in 2002, but broke up soon after.) Spalding then moved to Boston to attend the Berklee College of Music; upon graduating, at age twenty, she wrote and recorded Junjo.

“I’m very much ‘Don’t tell me what to do, don’t try to fuck with my art,’ ” Spalding admits, noting that having a strong sense of what you want can sometimes come off as harsh — not at all a bad thing, in her mind. “That layer of bitchiness can protect the vulnerability of a hit of inspiration,” she says. “You’re in a super-vulnerable state when you have an idea,” which makes advocating for that idea hard, especially “when you’re surrounded by people who are older than you, have more money than you, more of a track record of doing something that’s ‘successful.’ ” She continues, “It’s hard to say to those people, ‘I’m sorry, guys, I know you all think this is how this should go, but I don’t want to do it that way.’ ”

It’s for this reason that Matthew Stevens, Spalding’s electric guitarist, says she will only hire people she trusts artistically. “Because she’s put her implicit confidence in you, she is really inquisitive about what you think. She’s inclusive and inviting in that way,” he says. Stevens began working with Spalding two years ago, at the inception of Emily’s D+Evolution, when each track was still a demo, with her upright bass recorded on her iPhone. “We [her band] were involved from the ground floor. We had great adventures figuring out how we were going to bring it to life.”

Despite never having wanted to be a vocalist (“It just happened that way after joining the band,” she insists), Spalding sings with an almost incandescent joy onstage. Her soaring voice commands as much attention as her eclectic sartorial choices — mismatched prints, fringed pants, gold Lurex tops, and feathered crowns — which are increasingly sending little tremors through the fashion industry. Though she doesn’t “really know” what her style is, she often focuses what she opts to wear onstage around a theme. For her performance at the Kennedy Center, where she covered Sting’s 1988 hit “Fragile,” a tribute to an American civil engineer killed by the contras while working on a hydroelectric project in Nicaragua, Spalding chose a yellow gown to symbolize the canary in the coal mine — her own prescient warning about escalating political violence.

Off-duty, those choices are a lot less philosophical. “I pick the shirt at the top of my drawer and challenge myself to make an outfit of it,” she says. “I try to figure out how I’m going to make it sing — to put together an outfit that makes me feel good and that resonates with me that day.” Spalding, who grew up in Portland’s lower-middle-class King neighborhood (her mother worked several jobs to keep the family afloat), credits her unique style to a lack of access.

“My friends all had beautiful clothes, but I just couldn’t afford to find the real versions of any of those things. So I would do my own version of it with what I could piece together from the clothing bank or secondhand stores,” she says, simultaneously surveying the rest of the pieces laid out for today’s shoot. Fifteen years later, Spalding has found herself in a position where she “could go and buy those cool things.” But, she admits, “I prefer to go as me and see what that feels like.”

[This is part of the spring 2016 edition of Sheer, a quarterly style supplement by the Village Voice devoted to exploring and sharing the most dynamic elements of New York City’s fashion and design worlds, from the iconic to the as yet undiscovered. Check out the rest of Sheer’s featured stories here.]