Global sustainability challenges require a more responsible approach to production and consumption patterns on a global scale. One of the industries under observation is the textile and fashion industry. The chapter highlights the critical role of communication about sustainability and circular economy, and in particular the important contribution of video storytelling through the long-form documentary. After a background, the chapter presents and analyses the case of a documentary on a story of excellence in the field: the circular economy system in the Prato textile district. In Prato used clothes have been transformed into regenerated yarns to be used for new creations for 150 years now. Such regeneration process is able to create materials upcycling, combining tradition and modern technologies. The chapter analyzes the context, the documentary structure, content, and style, providing reflections for similar video storytelling projects.