This article argues for an updated theoretical framework in fashion studies. It proposes that perspectives emphasizing the social role and the technological nature of dress should be considered complementary, and that their joint application can contribute to new understandings of fashion history. Employing ethnographic methods, this stance is explored through a comparative analysis of the sartorial practices of two groups of women living or working in Amsterdam during the 1950s and the 2010s. A theoretical framework integrating theories of identity (mainly based on the writings of Georg Simmel and Gabriel Tarde) and the philosophy of technology (in this case the device paradigm of Albert Borgmann) allows us to uncover a paradoxical history of fashion in which clothing shifts roles, transforming from “things of imitation” into “devices of differentiation.”