This thesis explores the encounter between English colonists and Native Americans through the lens of “nakedness” and sartorial interaction in the 17th century. This thesis examines the spectrum of portrayals created by the English of indigenous bodies and adornment, identifying the variances and contradictions in how the English developed their understanding of the Other. Sartorial interactions extended beyond the gaze as English colonists and Native groups engaged in cycles of trade. This thesis traces the development of sartorial exchange after the early period of encounter into an era marked by war. Conflicts discussed include the Anglo-Powhatan wars, Pequot War, and King Philip’s/Metacom’s War. Gifting and stripping are highlighted as forms of sartorial interaction during wartime. Stripping, in particular, emerged as the bodies of soldiers, interpreters, and captives navigated the North American landscape of battlefields. This thesis attempts to question the levels of cultural cross-dressing and sartorial diplomacy that resulted from these interactions, analyzing how clothing and appearance were connected to colonial power dynamics in this period.