This chapter constitutes a close reading of the diaries and letters of Anne Langton (b.1804), a gentlewoman settler who migrated from Britain to colonial Upper Canada (what is now the province of Ontario) in the 1830s. Focusing on Anne's writings from her first ten years in Upper Canada, it considers how her sense of self, particularly her gendered identity, was challenged by the practices and daily routine of this new life. Notions of feminine gentility Anne brought with her were not always compatible with the nature of colonial society, and it is these discrepancies that will be explored. It is argued that Anne immersed herself in arranging and decorating the family’s new home according to dominant notions of civility and comfort in the hopes of resolving these conflicts. What is more, the act of writing about these activities, describing them in detailed letters to relatives in Britain, were fundamental to this process. This assessment draws on a variety of secondary literature and theoretical frameworks, principally those that sit at the intersection of gender studies and women's history, colonial and post-colonial studies and material culture studies.