This dissertation explores humanism, the rediscovery of the culture of ancient Greece and Rome, in late fifteenth- and early sixteenth-century England. It does so with reference to texts, institutional settings, and networks both within and beyond England, and examines the activities of several seemingly minor figures who have been absent from recent scholarship on the topic: John Holt, William Lily, Richard Croke, Leonard Cox, and Thomas Lupset. These figures made distinctive and original contributions to the genres in which they operated, whether the grammatical manual, educational treatise, dialogue, or philosophical meditation. They are also noteworthy for their considerable influence, whether in England or further abroad. With regard to Croke and Cox, the integration of previously unknown sources from France and Germany and overlooked ones from eastern Europe reveals that England could be an exporter and not merely an importer of humanism. Taken together, these individuals demonstrate that English humanism was more sophisticated and complex than its frequent characterisation as 'Erasmian' would suggest. In addition, this dissertation analyses the influence of humanism on two school foundations: St Paul's School and Ipswich College. It re-evaluates the portrayal of John Colet as an anti-intellectual, and understands St Paul's as a deeply personal endeavour, reflecting his desire to do better for the next generation. It establishes the depth and significance of humanism in Cardinal Wolsey's foundation of Ipswich College, hitherto accorded less importance by historians than his Oxford college. The examination of the little-known materials he published on the eve of his fall in 1529, together with reports from staff on its progress, show that he regarded it as central to his ambitious vision for England and to the creation of his own reputation as a civic humanist. This research therefore revises our understanding of a neglected period, and engages with the vexed questions at the heart of the study of humanism: how contemporaries dealt with the tension between their faith and their enthusiasm for pagan culture, and regarded the rival attractions of scholarly leisure and active public service.