This dissertation is a hermeneutic close reading of a single term—character. The term quickly became prominent at the end of the eighteenth century in landscape and architecture writing in English, but it did not have a clear definition at the time, and it has not yet been the subject of an extensive study to explicate its meaning. This study approached the problem through the selection of four exemplar authors, Thomas Whately, Humphry Repton, John Ruskin, and A.J. Downing, who produced some of the period’s most significant writing that employs the term. Every single use of the word character in works by these authors was evaluated for its meaning, either as defined or as suggested by context. From this extremely granular study, a system of connotations was derived. Three primary glosses of character, all pointing to different aspects of landscape and architecture, were in use, often at the same time and in the same works. I have called these connotations: enthrallment character, which is related to the moods that arise from a landscape or garden and has its roots in the British aesthetic tradition; accommodation character, which is used to describe the qualities of a place that signal that it meets domestic purposes comfortably; and identity character, which is the belief in a congruity between the character of inhabitants themselves and the character of their habitations. Chapters devoted to each connotation elaborate the substructure of the term, as usage reveals that authors had a concrete sense of what elements or dynamics in a landscape or building generate each kind of character. The three distinct meanings, with their own specific internal rules for generation, are united, however, by their structural dependence on propriety, specifically the notion of things fitting together appropriately. The mechanisms of propriety assure that character is legible and experienceable, even for the lay inhabitant.