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Fashion has become inextricably linked with digital culture. Digital media have opened up new spaces of fashion consumption that are unprecedented in their levels of ubiquity, immersion, fluidity, and interactivity. The virtual realm continuously needs us to design and communicate our identity online. Unfortunately, the current landscape of digitised fashion practices seems to lack the type of self-governing attitude and urgency that is needed to move beyond commercially mandated platforms and systems that effectively diminish our digital agency. As transformative power seems to be the promise of the virtual, there is an inherent need to critically assess how digital representation of fashion manifests online, especially when these representations become key mediators within our collective and individual public construction of self. A number of collectives and practitioners that actively shape a counter movement, organized bottom up rather than through capital, are questioning this interdependence, applying inverted thinking and experimenting with alternative modes of engagement. Starting from the research question ‘How can critical fashion practitioners introduce and amplify digital agency within fashion’s virtual landscape through new strategies of aesthetic engagement?’, this project investigates the implications of fashion’s increasing shift towards the virtual realm and the ramifications created for digital agency. It centers on how identity is understood in the digital era, whether subjects have full agency while expected to construct multiple selves, and how online environments that enact as playgrounds for our identities might attribute to a distorted sense of self. By using the field of critical fashion as its site, and the rapidly expanding frontier of digital counter practices as a lens, the aim of this project is to contribute to larger changes within an increasingly global and digital society, such as new modes of consumerism, capital and cultural value.