Fashion education needs to be rethought in light of the contemporary cultural, technological and social context. With the advent of AI and the uncontrolled production of images, one of the main challenges is to recover the historical dimension of fashion and to better exploit archival materials. To achieve this, we need to identify collaborative practices that bring together various disciplines and approaches, generating knowledge and sharing values, while producing culturally and socially sustainable products and narratives. To reflect on this, this paper analyses the experience of the workshop “Weaving Archives: Activating Textile Archives Through Artificial Intelligence”, promoted by the Master’s Degree in Fashion System Design of the Department of Architecture—University of Florence, in collaboration with the Master’s Degree in Fashion Studies of the Department of Arts—University of Bologna and the Fashion Research Italy Foundation in Bologna. The aim is to demonstrate how collaborative workshops provide valuable opportunities for training future professionals to balance the global reach of fashion with its complex local implications. This endeavour seeks to chart alternative paths that illuminate the intricate expanse of the modern fashion landscape.