This paper focuses on the teachings and admonitions regarding wisdom found in the sixth edition of Adam Smith’s Theory of Moral Sentiments (TMS). Following a mind-path marked by the seminal contributions of Glenn Morrow (1923), Donald Winch (1978), and Laurence Dickey (1986), the paper offers an interpretation of the higher moral standard (superior prudence) introduced by Smith in the last edition of TMS, as his response to the socio-economic and cultural changes that took place in Great Britain in the second half of the eighteenth century. Between the first and last editions of TMS the taste for luxury and conspicuous consumption became widespread and contagious both geographically and across ranks. Prudence and other-approbation, sufficient gatekeepers of moral conduct and character in the previous editions of TMS, became progressively less effective in keeping society away from moral deception and in regulating reputation and the distinction of ranks. The paper examines the introduction of superior prudence in the last edition of TMS as Smith’s vision of a dialectical process between external and internal approbation that is capable of transforming individual dependence on social praise into a dialogue between materialistic and moral concerns, which would lead to a progressively wiser, although conflictual, existence.