McKeown began her career in the folk scene. She released her first album, Monday Morning Cold, on her own label (TVP Records), travelling throughout New England while still a student at Brown University in order to promote the record. Although she had begun studying ornithology, she graduated from Brown with a degree in ethnomusicology.
McKeown's music is difficult to categorize in terms of genre; it has touched on pop, swing, rock, folk, and electronic music, as well as many other genres. Mckeown cites The Hitchhiker's Guide to the Galaxy as an influence on her music.