My thesis examines the sociolinguistic notion of prestige in the context of sixteenth-century Italy, with reference to the dynamics which arose between Tuscans and non-Tuscan learners over the ownership and nature of the literary variety based on fourteenth-century Florentine that was being codified and promoted. The notion of prestige is investigated by focusing on the relationship between: prestige and standard; prestige and context; prestige and social networks. My thesis brings together investigation of metalinguistic sources to reconstruct language attitudes (chapters 1 and 2) and the analysis of a corpus of correspondence to reconstruct actual usage (chapters 3 and 4). Chapter 1 employs a ‘new speaker’ paradigm borrowed from the field of endangered languages to explore the dynamics between Tuscan and non-Tuscan writers in early modern Italy, and the prominent role played by the latter in the codification of the literary variety. Focus is placed on the different prestige targets of non-Tuscan learners, on the problematic reception of the archaising ‘standard’ in Florence, and on the way prestige came to be attributed to the standard through a process of interaction between different groups of language users. Chapter 2 focuses on the importance of context when it comes to assessing the prestige or stigma attributed to the codified Florentine variety. Chapters 3 and 4 move to the analysis of usage, focusing on a corpus of Tuscan correspondence produced by the network surrounding the artist Michelangelo Buonarroti and his family members (1496–1585). The diachronic and diastratic analysis presented in chapter 3 reveals the gradual emergence and the social embedding of a range of codified, archaic Florentine features in the informal written language of a group of Tuscans in the course of the sixteenth century. In chapter 4, this macro-analysis is complemented by a micro-level approach which examines the language of individual members of one generation of the Buonarroti family. The network structure of each writer is reconstructed and related to their acceptance or resistance of archaic Florentine features. This chapter aims to integrate prestige explanations within a social network model. My project aims to offer a contribution both to our knowledge of the history of Italian and to the field of historical sociolinguistics. The rich metalinguistic documentation, the relatively high literacy rates and the abundance of written sources documenting usage make early modern Italy fertile ground for historical sociolinguistic investigations. Moreover, Italian is an interesting case-study as it appears to stand out from other linguistic traditions for the prominent role that has often been attributed to normativity in the development of the language.