The article briefly examines the phenomenon of Dandyism from multiple perspectives: historical, social, cultural and sexual, identifying the main values of aesthetic autonomy and individual personality in the 19th century in relation to the phenomenon of Metrosexualism as a consequence of a post-industrial, capitalist culture. The presentation is centered on the main characteristics of these two phenomena investigating them in terms of taxonomy, geographical diffusing, influences at the social, cultural and psychological levels, impact on influential historical figures and nowadays society, as well. The article employs the most prestigious figures of each category – Oscar Wilde, as a representative of the dandyism and David Beckham considered being the world’s top-rated metrosexual – and their contribution to a new form of aesthetics, but also the contexts mirroring the lifestyle, attitudes, movements, behavior, and symbols involved in outlining such stereotypes. The article is also focused on the description of the major differences between the two stereotypes employed, but also on revealing the differences and what actually makes them pertinent to be quantifiable. The entire debate is built around two core questions: (1) what exactly was the trigger or the necessity for such phenomena to come into being?; and (2) at which extent can these phenomena be related to a personality disorder?