Cross-gender brand extensions are a developing and valuable strategy that has quickly grown to become a vital component of strategic communications management. The goal of this study is to gain a greater insight on what makes for a successful cross-gender brand extension. In order to expand upon the Basic Model of Brand Extension Evaluation (Doust & Esfahlan, 2012), this study examines how marketing factors, more specifically product positioning, combined with consumer gender roles and brand concept, affect how consumers evaluate cross-gender brand extensions. In the past gender and brand concept have been studied within cross-gender brand extension research. Yet, the present study focuses on gender roles, conceptualizing gender as levels of masculinity and femininity. The products featured were positioned as having either a symbolic or functional brand concept. The results from this study not only confirm that gender and gender roles are indeed two distinct concepts, but they also indicate that gender roles and brand concept have a significant effect on brand extension evaluations, especially when level of masculinity is a factor.