The article is devoted to the phenomenon of monosandalism in ancient literature and art, which as yet has not been sufficiently researched. The author distinguishes three groups of mythological characters who are traditionally presented as wearing only one shoe (μονοκρήπις, μονοσάνδάλος), defining in this way various sources of such an approach. The first group includes the heroes whose monosandalism is justified by the mythological plot (Jason, Hermes, Lycurgus, Theseus). Second comprises the peoples who, for practical considerations, used to fight or hunt in a single shoe, while the third embraces persons (Dido) whose justification of monosandalism seems to have ritual grounds.