This paper analyses the results obtained from an online learning experience, in which fashion professionals and students were invited to explore and use a set of technology-based tools to develop their projects. It was expected that these tools and resources would potentiate and create a contextualized online learning experience in fashion design, helping learners to think and learn with each other, to bring ideas to life while interacting with data and information that were made available to them. A set of tools and resources were researched, identified, and allocated with specific fashion-design tasks. Participants were then asked to resolve these tasks resorting to the tools and resources presented and exploring beyond them, experimenting with potential uses in fashion design projects. The aim was also to understand if learners would acknowledge their potential to create a learning community, through connectivity and shared goals, helping them to develop their projects and stimulating reflective-thinking and self-determined capabilities, needed in the fashion professional environment. The results demonstrated that although learners recognised the potentiality of these tools for their fashion design projects, by convenience or lack of technological skills, they resorted to traditional methods of developing and communicating their projects. The results also demonstrated that like any technology adopted for educational purposes in the past, technologies-based tools, collaborative and mobile technologies require a further discussion about their limitations and potentialities and further experimentation by the fashion design sector.