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Most emerging Chicago artists have to make the decision at some point in their careers: Should I stay or should I go? For Tasha Viets-VanLear, the indie singer-songwriter who performs as the mononymic Tasha, the choice arrived under unique circumstances. In 2023, the Albany Park native, who by then had two well-received folk-inflected albums under her belt, auditioned for the nascent show Illinoise, inspired by the songs of Sufjan Stevens.

With her fluid vocals and nimble guitar playing, she won a role in the tight ensemble of actor-musicians. After workshopping the show that summer at Bard College in upstate New York, she returned home to a job at a wine store. “I was sort of mulling things over and figuring out what my future was going to be,” she recalls.

Then a twist: The musical took off after making its debut at Chicago Shakespeare Theater in early 2024. Off-Broadway and Broadway runs followed, as did a Tony for its choreography. The whirlwind experience convinced Tasha to move to New York City permanently to further her career. “My life certainly doesn’t look like that anymore,” says the 33-year-old, who now resides in Queens. “But it was enough information for me to make the decision that there was more for me to explore and figure out. There’s sort of a guilt one can feel — like you’re leaving people behind. So this really felt like a personal decision. I was doing something in my best interest, for my dream, my happiness, my ability to thrive.”

The change elicited new facets in her music, as heard on her fourth album, You Are Spring!, released in June and partly inspired by the Gwendolyn Brooks poem “To the Young Who Want to Die.” This ode to renewal leads off with “Spring,” a 76-second track featuring L’Rain and Chicago’s Jamila Woods in a cappella harmony with Tasha. It’s a gripping opening, setting the tone for an album that is at once introspective and joyful. —Britt Julious

Chicago-born singer Tasha modeling the top looks for fall 2026. (Christopher Semel/for Chicago magazine)
Left: Louis Vuitton cashmere turtleneck with leather braid trim, $4,800, and leather skirt, $4,150, 919 N. Michigan Ave. Right: Prada Shetland wool zip cardigan, $2,800, zip-front satin dress with built-in knit scarf, $5,400, rose-embroidered socks, $1,350, and jeweled slingbacks, $2,050, 30 E. Oak St. (Christopher Semel/for Chicago magazine)

On leaving melancholy music behind: “I have a lot of sad music, songs that have come from places of hurt or pain. I love what this music feels like and the purpose it serves. But I was excited about writing songs that were tethered to joy, to ideas of pleasure and flourishing and happiness.”

Chicago-born singer Tasha modeling the top looks for fall 2026. (Christopher Semel/for Chicago magazine)
Gucci python leather bomber jacket, $16,000, jersey boxer shorts, $490, leather Boulevard stiletto boots with horse bit detail, $3,000, and Dionysus bag, $3,350, 900 N. Michigan Ave. (Christopher Semel/for Chicago magazine)

On Legion Park (a site for this photo shoot): “It’s behind my former high school, Northside College Prep. Sometimes I’d hang out there after school, or go on walks through the park with my family’s dog. It’s really significant to me.”

Chicago-born singer Tasha modeling the top looks for fall 2026. (Christopher Semel/for Chicago magazine)
Bottega Veneta leather tank top, $5,900, and wool and linen trousers, $1,500, 41 E. Oak St. Victoria Beckham Tilly cotton T-shirt, $250, Neiman Marcus. Giuseppe Di Morabito rhinestone rose pin, $1,170, and Rochas leather gloves, $310, Ikram, 15 E. Huron St. Saint Laurent leather Splendor slingbacks, $1,550, 11 E. Walton St. (Christopher Semel/for Chicago magazine)
Chicago-born singer Tasha modeling the top looks for fall 2026. (Christopher Semel/for Chicago magazine)
Loewe napa leather dress (price not yet available), 51 E. Oak St. 6397 ribbed wool turtleneck, $395, Ikram. (Christopher Semel/for Chicago magazine)

On expanding her musical horizons: “I started playing clarinet last year. All of the clarinet on the record, I recorded myself. It’s opened up my ideas of what kind of musician I can be, and what kind of music I want to make, and allowed me to be more creative and experimental and expansive.”

Chicago-born singer Tasha modeling the top looks for fall 2026. (Christopher Semel/for Chicago magazine)
Zomer sequined backless dress with velvet straps, $1,060, Rochas leather gloves, $310, and Miu Miu nylon and python trainers, $1,575, Ikram. (Christopher Semel/for Chicago magazine)

Britt Julious is a freelance writer for Chicago magazine.

Styling: Patric Chauvez. Hair and makeup: Cammy Kelly/Distinct Artists. Set builder: Paul Igoe. Photo assistant: Edwin Menacho