The study of rhetoric has recently undergone a revival in political theory as a response to deliberative democratic approaches that value reason over affect in the political sphere. Most rhetorical revivalists look to Aristotle and develop accounts of ethos (character) that privilege the epistemic dimensions of trust, while overlooking the importance that considerations of propriety play in shaping the political speech of democratic leaders. We reconsider the rhetorical approach by integrating the regulative standards suggested by two political thinkers who also were theorists of rhetoric: Cicero and Adam Smith. Committed to character's role in collective judgment, Cicero and Smith both hold that sincerity and context shape decorum or propriety: Leaders rely on decorum to shape their rhetorical appeals, and audiences look to the fit between speech and character to gauge moral trustworthiness. Smith, however, goes beyond Cicero to develop a rhetorical theory more relevant for democracies by highlighting the importance of political context for rhetorical appeals and evaluations. We conclude by suggesting that attention to these components of decorum moves beyond Aristotelian accounts of rhetorical character in a way that is consistent with much empirical research on how voters judge the character of elected officials.