Born in 1994, Swift grew up in Charlottesville, Virginia, the daughter of noted jazz pianist Hod O'Brien and jazz singer and educator Stephanie Nakasian. Introduced to jazz at a young age, she developed quickly as a performer and was soon playing alongside her parents. When she was nine years old, she made her recorded debut with Veronica's House of Jazz, which featured her parents and saxophonist Richie Cole. At age 11, she performed as part of the Women in Jazz series at Dizzy's Club Coca-Cola in New York City, and at 13, she issued her sophomore album, It's Great to Be Alive, with saxophonist Harry Allen. From 2013 to 2014, she further honed her skills studying at the Frost School of Music at the University of Miami.
In 2015, Swift gained wider acclaim after finishing second place in the prestigious Thelonious Monk Jazz Competition. That same year, she released Lonely Woman, featuring her band with pianist Emmet Cohen. Showcase performances followed, including a 2016 concert at the Tribeca Performing Arts Center, a guest spot with Michael Feinstein at Jazz at Lincoln Center, and a headlining performance at the 2016 Telluride Jazz Festival. The following year, Swift held down a residency at Birdland Jazz Club in New York City, and collaborated with saxophonist Jeff Rupert for the album Let's Sail Away. She has toured with pianist Benny Green, Wynton Marsalis and the Jazz at Lincoln Center Orchestra, and trumpeter Chris Botti, among others.
Swift made her Mack Avenue debut with the 2019 standards album Confessions. Featuring contributions by both Emmet Cohen and Benny Green, the set cracked the Top Five of Billboard's Jazz Album chart. In 2021, she returned with a genre-bending album of covers, This Bitter Earth. ~ Matt Collar, Rovi