It is our strong believe that fashion, more specifically apparel can support us so much more in our daily life than it currently does. The invention of Cliff, an automatized zipper, is a response to the struggle by elderly, people with physical disability, children, athletes, and ladies who have problems zipping back-zipper dress. Fashion-oriented design encourages ingenuity, imagination and innovation , which are crucial elements in pushing forward technological and social progress. This project is inspired by Adam Whiton, who developed the Zipperbot, and the educational module ‘actuating movement in refined wearables’, published at the Global Fashion Conference 2014. Realizing that the Zipperbot is not generic, the Cliff project takes this gap as an opportunity to create a universal robotic zipper. A detailed review has been conducted to understand the physics and mechanics of the zipper. An iterative “research through design” approach was used during the development stage of the Cliff. The prototyping stage involved several iterations towards the development of a working mechanism and ended with the miniaturization of the Cliff prototype. In between the iterations, the stakeholder and user feedback obtained from exhibitions has been used for the next iteration of the design. The early prototyping stage of Cliff has used Meccano to explore traction mechanisms. Afterwards 3D rapid prototyping was used to manufacture and miniaturize the prototype. Again, we developed a working prototype and a short video. Problematic is that wearable systems are almost exclusively discussed with a functional focus. The functional benefit is entirely lost if a user refuses to adopt the technology because of social factors. Dunne (2015) argues that the social facet of “wearability,” the variables and factors that influence how socially comfortable an individual feels while wearing a piece of technology, is crucial to user adoption of a technology. Cliff’s functional relevance is clear; it could be beneficial not only for elderly or people with physical disabilities but also for wearables in fashion. Now we have to start tackling the ‘social wearability’ of this system. The development progress of Cliff shows huge potential of developing a generic automatized zipper and it might be the “future of fashion” in smart clothing or wearable technology when taking social aspects into account. For future works, the technology, user focus, and fashionability need to be improved including the aesthetic elements and functionality, depending on its context of use.