The current economic and financial crisis is forcing a rethinking of dominant economic models and, at the same time, triggering innovative socio-economic processes. Over the past years, in the fashion and design industries several interesting experiences have emerged that partially recover traditional strategies, yet innovate thanks to digital technologies. The goal of this paper is to reflect on the relationship between fashion, design and new technologies, and those intersections between them that are increasingly labeled with expressions such as digital fabrication, wearable technology, or fashionable technology. The advent of digital technology has led to significant innovations in modes of production, sales, communication and consumption; innovations that can transform not only tastes and lifestyles but also offer real prospects for a sustainable and fair future.