Hilary Gardner grew up in Wasilla, Alaska — jazz's least likely hinterland — but by her own description was "a New Yorker at heart" long before she ever saw the city. She sang in the Alaska Children's Choir, studied classical voice, and performed with the Anchorage Opera as a teenager, while moonlighting in local bars singing country standards. The voice that pulled her toward jazz was Ella Fitzgerald's, especially Ella Fitzgerald Sings the Cole Porter Songbook; she has also named Patsy Cline, Aretha Franklin, Joni Mitchell, and Tom Waits among the singers who shaped her ear.

After stints in Italy and Seattle, Gardner arrived in New York City (settling in Brooklyn) in 2003. Getting there was one thing; establishing herself as a jazz singer was another — she supported herself waiting tables for roughly a decade before her recording and performing career could stand on its own. That career now spans four studio albums under her own name (Have Yourself A Merry Little Christmas, 2004; The Great City, 2014; The Late Set, a duo record with pianist Ehud Asherie, 2017; and On the Trail with The Lonesome Pines, 2024), plus a 2019 duo tribute record with drummer Charles Ruggiero, Play the Bird & the Bee. DownBeat has named her a Rising Star Female Vocalist five times in its annual critics poll and called her "an artist to watch," while The New Yorker described her as "a singer with a beguilingly subtle wit."

Gardner's highest-profile theatrical credit came in 2010, when the Frank Sinatra estate selected her as the live, onstage vocalist for Twyla Tharp's Tony Award-winning Broadway revue Come Fly Away, which ran at the Marquis Theatre from March to September of that year. Backed by a nineteen-piece big band, Gardner sang solos and duets against recordings of Sinatra's own voice — a role that required matching phrasing and dynamics to a ghost, night after night, to widespread critical acclaim. She has gone on to perform with symphony orchestras nationally, serves on Juilliard School's jazz voice advisory committee, has sung at New York Fashion Week for designers Ralph Lauren and Naeem Khan, guested with actor Jeff Goldblum at Café Carlyle, contributed vocals to a Moby recording, sung the national anthem at a Mets game, and appeared in Errol Morris's 2017 Netflix docudrama miniseries Wormwood.

Gardner is a founding member of Duchess, the close-harmony vocal trio she formed in 2013 with fellow Anzic Records labelmates Amy Cervini and Melissa Stylianou, built around three-part arrangements modeled on the Boswell Sisters (and, by some accounts, the Andrews Sisters) rather than the solo-vocalist-plus-rhythm-section format of most of her own leader dates. Duchess released its self-titled debut in 2015, followed by Laughing At Life (2016/2017) with guest turns from Anat Cohen and Wycliffe Gordon, a Harmony for the Holidays EP (2018), and Live At Jazz Standard (2020), recorded over two nights at the since-closed Manhattan club. The trio has toured major festivals including the Ottawa Jazz Festival, Toronto Jazz Festival, Xerox Rochester International Jazz Festival, Saratoga Jazz Festival, Monterey Jazz Festival, and the Jerusalem Jazz Festival, and won Vocal Group of the Year at the Jazz Journalists Association Awards in both 2021 and 2022, plus Best Vocal Group in JazzTimes' 2021 critics poll. After a six-year gap, Duchess released its fourth studio album, A Marvelous Party, on Anzic Records in June 2026 — a concept record tracing one night out through Rat Pack-era standards, expanded for the occasion with a small horn section arranged and produced by longtime collaborator Oded Lev-Ari.

Gardner's most recent turn as a leader moved in an unexpected direction: On the Trail with The Lonesome Pines (2024) reframes 1930s-40s "singing cowboy" repertoire — the Sons of the Pioneers tradition — as vocal jazz, produced by Eli Wolf. The record was named one of The Times of London's top 10 jazz albums of 2024, drew a "something new and wondrous" from The Wall Street Journal, and won the 2025 Western Heritage Award for Outstanding Traditional Western Album from the National Cowboy & Western Heritage Museum, as well as Album of the Year from the International Western Music Association — an unusual crossover honor for a jazz singer, and evidence of how far her Alaska-to-New-York arc has traveled.

Gardner works comfortably across at least three distinct modes: the intimate, songbook-grounded balladry of her Ella Fitzgerald-rooted solo records; the tight three-part close harmony of Duchess, which trades her own spotlight for blend and requires a different kind of vocal discipline entirely; and, more recently, the open-range balladry of the singing-cowboy tradition on On the Trail with The Lonesome Pines. Her two years standing in for Sinatra eight times a week in Come Fly Away left an audible mark — a phrasing patience and a comfort inhabiting other singers' melodic choices that carries into her own recordings. Critics have consistently pointed to wit and understatement rather than vocal pyrotechnics as her signature: The New Yorker's "beguilingly subtle wit" is the phrase that follows her most often, and it holds up across genres as different as Ladino-adjacent torch song and cowboy balladry.