This thesis draws together material and archival sources to investigate the long-overlooked portraits of English provincial gentry families commissioned between c.1550 and c.1680. Specifically, its focus is on portraits of family groups where more than one generation, connected through blood or kinship, is depicted in the same composition. The thesis identifies these as a coherent genre for the first time and examines the ways in which the gentry used such paintings to establish familial legacy and heritage for future generations. This thesis explains how these portraits respond to, and reflect, family memory and narratives, social networks, local histories, religious observance and artistic developments. They are important because the family, as the basic unit of society, was essential for the formation and transmission of belief and identity, and the place where children were socialised. The portraits simultaneously reflect broad social trends while also containing personal messages about the lives and relationships of individual families which were specific to their own particular place and time. The thesis argues for the significance of visual artworks and especially this genre of painting, in the construction of gentry status and self-fashioning over this key period of social change.