The turn of the new millennium with its numerous breakthroughs, transformations, novelties and technology having penetrated all spheres of the society left an impact on the field of contemporary fashion as well. The thesis approaches the relationship between (contemporary) fashion and technology in the age of technoscience from a different perspective, namely by considering transgression as the essence of contemporary fashion through the concepts of technoscience, society of control, cybernetics, contemporary fashion and ‘the cyborg myth’ introduced by Donna Haraway. Some current examples of contemporary fashion, a multidisciplinary approach to the topic and the application of various concepts indicate that the instability and uncertainty of the new millennium can be observed in the constant requestioning of boundaries between the dualisms originating in the Cartesian philosophy of mind and body, namely artificial – natural, reality – simulation/virtuality/fiction, signifier – signified, beautiful – ugly, human – machine, man (masculinity) – woman (femininity), haute couture – prêt-à-porter, and manual – mechanical; the boundaries between these dualisms are no longer fixed and clear — they have become transitory and dubious. Contemporary fashion considered as a fashion at the edge of boundary is thus a constant experience of transgression.