This paper explores the identity and social worlds of the ‘urban gentry’ of Chester as they developed from the late seventeenth to the mid eighteenth century. In place of the political and cultural definitions which characterise analyses of this group, it takes the self-defined ‘occupational ’ titles of probate records as a starting point for an investigation into the background and activities of those styling themselves ‘gentleman’. Central to their identity were networks of friendship and trust. These reveal the urban gentry to have been closely tied with both the urban middling sorts and the rural gentry: a position which at once reflected and underpinned their particular situation within eighteenth-century society