Utilizing Georg Simmel’s “oldie, but goodie” text Fashion (1904) as a convenient reference-point, I will critically discuss how some of Simmel’s original concepts (dialectical dualities) reappear in newer theories of fashion. I will also make use of newer examples of theory application by colleagues as well as in some of my own research. An especial point will be made of problematizing some of the theoretical assumptions, which are brought up in the discussion. Among Simmel’s concepts, each of which will be explained and then problematized by a contradictory ‘case’, are his “imitation vs differentiation” assumptions of fashion diffusion processes (case: Mao and Nehru tunics); “union vs. exclusion” (case: the Jewish presence in Punk); equalization vs. individualization (case: African-American stylin’); appropriation (case: from Levantine fashion in ancient pharaonic Egypt to Sun Yat-sen suits); values attached to fashion(s) (case: Kopytoff’s fashion ‘life stories’); outré and anti-fashion fashion as desire for destruction (case Incroyables/Merveilleuses and ‘Rock Military Style’); fads (case: Davy Crockett coonskin caps); and fashion novelty and transitoriness on the dividing-line between past and future (case: Karl Lagerfeld’s (re)styling of Chanel). I shall also deal with Bourdieu’s charting of the competitive playing field of French postwar fashion (case: Karl Lagerfeld as an individual fashion ‘player’ within Bourdieu’s field structure). This leads up to a brief description of a biographical approach to the analysis of fashion designer creativity, focusing on the phenomenon of ‘creative tension.’