This dissertation examines how early modern writers deployed figures of similarity and arguments of similitude in textual and visual representations of Native American women in trans-Atlantic texts about the Americas. I explore the relationship between representations of English and Native women by investigating the ways English authors link the two figures through comparisons that reveal similarities. English writers asserted shared traits between Native and English women to cast indigenous peoples as potential subjects of the English crown. However, these writers did not describe processes of assimilation or acculturation: the English represent the Natives as already like them. English writers used similarity between Native and English to differentiate themselves from other European colonizers in the Americas, to provide rationales for possessing American land, and to reassure English investors and would-be colonists of the safety and stability of the relationship between Native and English. My introduction situates early modern arguments of similarity and similitude alongside contemporary notions of fluid racial and cultural identities. Chapter 1 examines the descriptions of the Native woman captive in George Best's travel narrative about the Frobisher voyages and the rhetoric of similarity between Native and English women employed in this description; this rhetoric enables Best increasingly to include England's own Elizabeth I as a central character in support of the voyages. Chapter 2 considers Sir Walter Ralegh's use of the figure of the Native woman to make an analogical rhetorical argument comparing Elizabeth I to Native women rulers and, thus, to argue for English claims to American land. Chapter 3 examines how Aphra Behn and Mary Rowlandson reflect changing attitudes about Native Americans through their use of similarity to convey colonial anxieties about safety and cultural degradation as opposed to earlier depictions of similarity to convey a reassuring statement of colonial peace.