This chapter discusses the relationship between spelling and writers’ social background, identifying how access to literacy and literacy practices in the history of English contributes to the spelling forms and conventions used in historical texts. It provides an overview of spelling and literacy in Old and Middle Englishes. Gender and social status inflect the spelling evidence from these periods, with the historical manuscripts largely representing the orthographic preferences of elite men, typically linked to religious houses or royal administration. More recent periods provide a broadening picture as access to literacy increases; nevertheless, when analyzing and interpreting historical spelling practices, it is important to recognize the potential skewing of any dataset. The chapter then surveys studies that have attempted to identify authorship on the basis of orthographic evidence. Citing examples from Shakespeare studies, it identifies the potential of this approach, and the need for caution when making pronouncements without an empirical baseline of spelling norms for a period. Finally, the chapter considers the relationship between gender and spelling in the history of English, highlighting negative social attitudes toward women’s spelling in a range of publications, and showing that claims made about women’s practices are not always borne out by empirical analysis.