"Motivation" is the force that drives an individual to perform a certain action. Abraham Maslow (1908-1970), an American psychologist profoundly influenced by the existential and teleological paradigms, expounded a motivation theory that remains precise and replicable, as well as applicable to other spheres of study, including the humanities. Indeed, psychology experts and non-specialists are by and large familiar with Maslow's Pyramid of Human Needs. Moreover, despite the abundance of literary criticism that utilizes Freudian-based theory to analyze the motivations of literary characters, critics have largely neglected the use of other paradigms, including Maslow's. In this thesis, I use Maslow's texts as support for identifying the motivations of women characters who dress as men in Shakespeare's dramas. I also simultaneously employ Maslow's theory to illuminate the parallels in these characters' motivations and the varying need levels that Maslow develops in his hierarchy. After a comprehensive review of the literary criticism that addresses the dramatic motif of cross-dressing in early modern England and an extensive explanation of the history of motivation theory up to and including that of Abraham Maslow, I treat the following plays by William Shakespeare: The Two Gentlemen of Verona, As You Like It, and The Merchant of Venice in conjunction with Maslow's Pyramid of Human Needs. Through this analysis, I demonstrate that Julia cross-dresses to satisfy needs on the level of Love/Belonging; Rosalind cross-dresses for reasons that correspond to the Safety level, then to the Esteem level; and Portia demonstrates motivations that correspond to Maslow's Love/Belonging and Esteem levels.