The volume presents a wide-ranging investigation of the ways in which Petrarch’s legacy informed the relationship between visual and literary portraits in sixteenth-century Italy. Petrarch’s vast literary production influenced the intellectual framework in which new models of representation and self-representation developed during the Renaissance. His two sonnets on Laura’s portrait by Simone Martini and his ambivalent fascination with the illusionary power of portraiture in his Latin texts — such as the Secretum, the Familiares and De remediis utriusque fortune — constituted the theoretical reference for artists and writers alike. In a century dominated by the rhetorical comparison between art and literature (ut pictura poësis) and by the paragone debate, the interplay between Petrarch’s oeuvre, Petrarchism and portraiture shaped the discourse on the relationship between the sitters’ physical image and their inner life. The volume brings together diverse interdisciplinary contributions that explore the subject through a rich body of literary and visual sources.