The aim of this text is to explore conceptually, within the specific spectrum of song, the possible approximations between fashion and literature. In addition, it aims to reveal the meanings attributed to certain items of clothing in Dorival Caymmi's work; and, as a consequence, to propose a reflection on the participation of the fashion system, clothing, material culture - and consumption - and the song itself as constituent, defining and dynamising elements of Brazilian culture. To this end, we began with a conceptual overview of the symbolic relationships between music and literature, followed by an analysis of the songs ‘O que é que a baiana tem?’, ‘Vestido de bolero’, ‘Requebre que eu dou um doce’, “Maracangalha” and ‘A vizinha do lado’. The analyses were able to highlight the dense meanings of fashion and its privileged place in the formation of the Brazilian imagination, as well as being a source of inspiration in artistic, musical and literary productions.