This article studies the portraits of two gender-ambiguous individuals, the seventeenth-century Spanish soldier Antonio (née Catalina) de Erauso and the eighteenth-century French diplomat the Chevalier (Chevalière) d’Eon, as they offer a window into early modern debates on the representation of nature through its wonders. Making sense of the representations of Erauso and d’Eon requires viewing them as depictions of nature that belonged to the genre of the cabinet of curiosities. When seen as part of the cabinet of curiosities, their paintings appear as part of the artistic and scientific explorations that negotiated changing concepts of nature in early modern Europe. While Erauso’s portrait belonged to a tradition that embraced the sitter’s gender ambiguities, d’Eon’s portrait appears instead as a transitional object between two ways of organizing knowledge of nature. D’Eon’s portrait reflected a grown interest in the eighteenth century of representing nature in an objective way with a clear separation between the genders.