Conor Oberst is an emotional songwriter who has always worn his heart on his sleeve, returning to favorite topics - drugs, love, politics, self-doubt - with a poetic flair that has earned the singer a devoted following across the various monikers he creates music under. "White Shoes" is Oberst at his most stripped down: simply the singer and a guitar, singing plaintive lyrics in a reduced, almost mournful tone.
Lyrically, the song is somewhere between a love letter and an ode. The verses are directed toward a woman that Oberst is in love with, and poetically it describes an allusive set of things that she could do that he wouldn't mind doing with her. These sketched images border on the surreal and dreamlike, creating a uniquely powerful sense of the degree of Oberst's affection. "You can get your hair all wet, sleeping on the riverbed," he croons, "kiss a frog and dissect, gotta find out what's inside," before moving onto the frequently refrained "anything you want to do; lover, anything you want to do."
Outer South was nominally Oberst's fifth solo album. However, the album is also accredited to The Mystic Valley band, an Omaha ensemble of musicians that has assisted Oberst on previous releases. This time around, Oberst decided to shift the spotlight to some of the other musicians. For the first time on an Oberst release, he didn't write all of the songs (almost half are credited or partially credited to bandmates). Additionally, the singer neglected to answer questions about the album's music in interviews, saying instead that the interviewers should question his bandmates.
A follow-up to the song, "White Shoes (reprise)," appears in the band's 2012 documentary, One of My Kind.