As the sustainable fashion movement gains momentum, there is a growing need to introduce such concepts to the next generation of fashion designer. One approach to produce sustainable designs is upcycling, defined as the salvage and reuse of discarded or found items into new products. This study examines a pedagogical approach for engaging 2nd year undergraduate textile and fashion design students in sustainable fashion design practice. Working in groups, students are challenged to upcycle old clothing into a little black dress, using a keyword as direction for concept, design development, and garment construction techniques. To elevate value in post-consumer textile waste, it is necessary to develop high-quality contemporary design outcomes. This teaching approach aims to encourage the revaluation of recyclable resources, the exploration of the creative potential of fabric manipulation techniques, experimental design development, and professional production techniques. This is achieved through the implementation of a design brief that establishes original approaches to upcycling, contrary to the arbitrary processes that are typically used.