Collaborations between fashion designers and artists, traced back to 19th century, bloomed in early 20th century when fashion became a modern desire and was mass producible (Mackrell, 2005). Due to the complexity and ambiguity of the wearable art design process, wearable art designers usually explore inspirations from a multiplicity of sources, sometimes drawing from fine arts. Collaborations often occur between wearable art designers and artists that contribute differential resources and various talents to achieve complementary goals (Dodgson, 1994). For this design process study, the initial goal was to develop a framework for: (a) initiating and completing collaborative design projects, (b) evaluating the design ideas involving a wearable art designer and an artist who provided the artwork as the inspiration, and (c) integrating a review critique into the design process by presenting design ideation to a professional reviewer (with fashion design and wearable art background), an industrial designer, and collaborating artist.