In early modern England and France, diverse literature, from pamphlets to poetry, links gender ambiguity to its ability to evade categorisation, blur boundaries or deceive. While previously gender ambiguity in art has often been dismissed as the product of historical distance, or discussed primarily in terms of sexuality, these literary and social contexts suggest that ambiguity was central to how contemporaries considered this subject. Drawing on recent literature on ambiguity in art, this thesis explores the potential of ambiguity as a period-appropriate context for studying early modern images of androgynous figures, cross-dressing, and gender transformation. By exploring, rather than resolving, their ambiguity, this thesis aims to shed new light on objects whose challenging effects have often led them to be oversimplified or set aside.

The first chapter places Francesco Primaticcio’s complex and ambiguous frescoes of Hercules Cross-dressing, c.1535, in the context of fascination with ambiguous images and their potential to spark learned discussions, feeding the socially competitive court of François I. The next two chapters use French renaissance and English Ovidian poetry to explore how two understudied depictions of androgynous sitters in the Triple Profile Portrait in Milwaukee Art Museum, c.1570, and The Cobbe Portrait of Henry Wriothesley, c.1590-1593, paralleled contemporary poetry that admired gender-ambiguous figures for their pleasurable capacity to confound expectations. The final chapter addresses how Jacobean prints and pamphlets targeted masculine women as a cipher for a range of social and political ambiguities produced by the legacy of Elizabeth I. These four case studies examine the possibilities of using cultures of enigmatology, and attitudes towards ambiguity, as a platform for understanding a variety of meanings that images of gender ambiguity could possess for early moderns.