This article investigates the way in which the English poor used the rhetoric of clothing in their engagement with local officials as they attempted to secure poor relief. Using letters written about or by the dependent poor from a wide selection of English communities, the article suggests that the poor employed concepts such as raggedness, lost clothing, nakedness, compromised dignity, and community presence and the link between poor clothing and unemployment, to assert their deservingness. An exemplar of a series of letters from the same person is used to explore how paupers developed the rhetoric of clothing over a sustained period of correspondence, suggesting that paupers had a keen appreciation of the impact of compromised clothing in their negotiations with officials. Ultimately, this paper will argue, paupers and officials had a shared concept of minimal clothing standards and a shared linguistic register for linking clothing and deservingness.