Sixteenth- and seventeenth-century portraits from the Italian peninsula that depict women with keyboard instruments have been discussed as an apparent trend by feminist art historians and musicologists. While the connection between these portraits and the well-known iconography of the musical St. Cecilia has been noted, the association between keyboard instruments and the female body has been less frequently explored. In this study, I use methodologies from feminist theory and gender studies, most notably gender performativity, in order to explore how an artist's dialogue between the portrait subject and her instrument creates and is created by complex relationships ingrained by the dominant patriarchal structures that circumscribed women's lives at the time. To realize these interpretive goals, I have chosen two paintings that are less often discussed in art historical and musicological literature: the self-portrait attributed to Marietta Robusti, and St. Cecilia Playing the Keyboard in the style of Artemisia Gentileschi.