From The Times They Are A-Changin', “Boots of Spanish Leather” takes the form of a dialogue between two lovers, one of whom is going away on a long journey. The theme of a bittersweet parting before a journey is common in folk songs – see for example Dylan’s cover of the old ballad “Farewell” and the traditional song “Blackjack Davey” which Dylan covered many years later.

Note the many striking similarities in both melody and lyricism to The Freewheelin' Bob Dylan’s “Girl From the North Country.” Many have theorized that the songs are linked in some way, though whether they are about the same girl is not definitively known.