A growing number of brands are proving luxury and sustainability can coexist. Consumers are demanding more eco-friendly practices, and increasingly the clean and essential style of Quiet Luxury is enforced in the fashion system. This chapter focuses on the textile district of Prato, Italy, and discusses its unique organizational model that has fostered flexibility and creativity in fashion collections over the years. One of the key elements of this model is the division of labour among many specialized small and medium-sized enterprises. For over a hundred years, Prato has leveraged the circular economy and embraced the motto “reuse, reduce, recycle”. It thus has a well-established tradition of sustainability, both environmental and ethical. Few consumers are aware of this tradition because communication of its sustainable practices has been neglected for a long time. Now, new consumption models require more detailed information, both on materials and production processes. Increased use of information technology and digitization of processes is urgently needed, but this will require a substantial investment. Considering that Prato’s businesses are small and medium-sized, will they be able to conquer this new challenge?