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Popular culture, especially cinema, tends to view the world of fashion from a distance, often in admiration but mixed with feelings of incomprehension, perplexion and even derision. The current article will analyse the films Pret-à-Porter (Altman 1994), Zoolander (Stiller 2001) and The Devil Wears Prada (Frankel 2006) as expressions of general approaches to the fashion industry in the comedy film genre. As high profile films, they embody a pattern of representation endemic to film comedy at the turn of the 1990s and 2000s and emphasize a frivolous, ironic attitude to the superficial and exploitative nature of the fashion industry, reflecting a wider sense of postmodernist cultural critique in American cinema of the shallowness of commercialism and pop culture (while, ironically, being part of precisely the same system as the target of its critique). By conducting narrative analysis of these films, we will show how they use stereotyping as a mechanism to satirize the fashion industry, creating superficial flashes of ridiculous behaviour and excessiveness, while they reinforce these approaches themselves through the use of genre and aesthetic conventions. In doing so, the films highlight the idea that fashion, as a form of popular culture, functions as an exemplary locus of cultural critique to satirize hyper-consumption and hyper-commercialism. As these films evoke wider questions about the concept of irony within and towards fashion, the chapter is a part of a larger project on the theme of fashion irony that aims at defining it as a field of academic study.