The early modern fairy is a long ignored transgender figure. This article presents a transhistoricist analysis of how a range of “transgender” concepts manifest in the early modern literary imagination—instabilities, transformations, ambiguities, or indeterminacies in sex and gender—through the representation of fairies and the supernatural. It focuses on Ariel in Shakespeare's Tempest, Duessa in Spenser's Faerie Queene, and Jocastus in Randolph's Amyntas. Breaking from the threatening fairies of the medieval tradition, early modern writers reshaped how fairies were conceptualized in popular imagination, which inform our ideas of the supernatural and gender instability to this day. While transgender approaches to the medieval period have recently come to prominence, transgender approaches to the early modern remain marginal. This article seeks to establish what early modern fairies offer transgender theory and what transgender theory can offer early modern historicism. Through transgender readings of fairies and supernatural figures, this article demonstrates how such figures provided a space in which early modern culture could fantastically conceptualize transgender concepts and identities.