There is a growing number of aging homeless women who are looking for shelter and struggling to construct a sense of valued life and self (Gonyea and Melekis, 2016). This concept paper presents a design approach that continues to engage underprivileged women in a cocreative design experience. The goal of this collaborative involvement was to inspire and positively impact the self-confidence of these women through use of their creativity in developing fashion products. The creation of these products would add another dimension to part of their job-training program. According to Csikszentmihalyi (1997) enhancing creativity through exploration and discovery may consequently improve well-being. Specifically, Prescott et al. (2008) found a strong correlation between art making activities and life achievements of the homeless. The women in this co-creative design experience imagined design ideas through a series of accessible creative activities.