Applying design process model as the framework during the creative process facilitates documenting the process in a method easy to interpret and replicate for other wearable artists or designers. Thus, the purpose of this research were to: (a) fuse the techniques of Chinese painting and art philosophy with contemporary garment silhouettes to create three lines of wearable art that are inspired by the three most prominent motifs found in Dafang Zhang’s (the researcher/designer’s father) Xie Yi painting, (b) propose a model outlining a design system for creating wearable art useful to other designers and artists based on documentation of the wearable art design, and (c) examine the methods of evaluating wearable art design regarding the comparison between self-reflection and professional evaluation.