Taking a nostalgic approach to covers of Christmas standards and carols, the singer worked with Dan Romer on most of the material.

Songs for the Season debuted and peaked at number 94 on the US Billboard 200 and became Michaelson's fourth consecutive top three entry on the Independent Albums.

[5] Drawing inspiration from Frank Sinatra, Nat King Cole, Judy Garland, and Brenda Lee, Michaelson envisioned an album "that was an instant, nostalgic classic" and would convey authenticity, warmth, and familiarity.

[4] Allmusic editor Matt Collar remarked that "rather than take the more common contemporary approach to her first album of holiday-themed music on 2018's Songs for the Season, singer/songwriter Ingrid Michaelson instead successfully wraps herself in an old-school production that sounds like it was recorded in the 1950s."

"[6] Jon Caramanica from The New York Times declared the album "polite and precise Golden Age Christmas carol revivalism."