“I feel so lonesome I could cry,” Angel Olsen sang on the gauzy country-grunge shuffle “Hi-Five” from her second album, Burn Your Fire for No Witness, one of 2014’s most haunting albums. Yet with that melancholic allusion to a country icon, the Chicago singer/songwriter found herself pigeonholed. “Suddenly I was this cartoon version of a honky-tonk girl, but I’ve only played one song that references Hank Williams,” she says. “I don’t really mind it, but it’s just not really how I see my music.”

With the pressure of public perceptions magnified by the success of that album, Olsen took stock of how she really saw her own music before making her sublime Sept. 2 follow-up, My Woman. Part of that process involved taking a break from music, followed by more relaxed touring through Turkey, Greece and Portugal, Olsen says. And when she began writing again, she approached some songs on the piano (her first writing tool while growing up in St. Louis) and synthesizer rather than just guitar.

“I realized I have a style, and my style itself is unpredictable,” Olsen says from her new home in Asheville, ahead of a tour with her sextet that hits the Sinclair on Sept. 20 and 21.

Granted, the 29-year-old hasn’t jumped off the deep end on My Woman, though there’s clearly an evolution, particularly from folky roots that included an initial stint as a backup singer with Bonnie “Prince” Billy. If anything pervades, many of the songs echo the sound of ’60s girl groups or doo-wop. “I did listen to a lot of doo-wop when I was growing up because my parents grew up during that time,” Olsen says, noting her love for the Everly Brothers and Motown records. “You just don’t hear that in modern music anymore.”

The first half of My Woman casts the starkest shifts for her, from the synth-cradled “Intern” to the retro-pop “Shut Up Kiss Me.” Olsen self-directed videos for those songs, in which she lip-syncs in a tinsel wig. And she indulges her passion for roller-skating in the sassy video for “Shut Up Kiss Me,” which includes an outtake where she asks the camera person, “Do I need to give more attitude or…?”

“Because my writing on the record—and my writing in general—can sort of be pretentious or intellectual in its way, people are afraid of ever letting me be light,” Olsen says. The wig, however, was an afterthought rather than some grand statement, she says, because she lacked the budget for a stylist to keep her hair consistent through the filming. “I was like, ‘David Bowie died, and I like Dolly Parton, and why not be a character?’ I was just trying to have fun.”

The album’s second half, on the other hand, gets introspective with longer, lyric-intensive songs. “I’m hardly ever literal,” Olsen says, describing those songs as “an open-letter style.” Foremost among them—and keeping with the album’s theme of gender—are the heartache-infused, spectrally sung “Woman” (where Olsen sings, “I dare you to understand what makes me a woman”) and “Sister,” which recalls Stevie Nicks’ early work with Fleetwood Mac as Olsen mulls the depth of a relationship, of being there for each other.

“I didn’t want it to be a romantic love, or not romantic in a typical way, so I named it ‘Sister,’ ” Olsen says. “It’s a feminine title, so I went with that. But I think in my head, it could be anyone.” And that, she adds, includes the idea that it could be herself.

“I’m talking a lot about love on this record,” Olsen says. “I’ve got people asking me, ‘Is it you? Are you the woman [of the album title]?’ And yeah, I’ve always been the writer of my work… Sometimes the way that you’re misunderstood is the way that people gain something from your work, so correcting them feels wrong too. For me, if people find meaning in it, great. If they think it’s a feminist work, fine. If that’s the case, [they] should look at all of my catalog. But for this particular record, I guess for the first time, I feel like I’m putting myself out there.”

Angel Olsen plays the Sinclair on Sept. 20-21.

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