This research project analyzes the history between fashion and art and investigates several recent collaborations between designers and artists, with the intention to distinguish the benefits each brand receives through the affiliation with one another. In today’s cultural and commercial market, there are an abundance of new collaborations between designer brands and artists continuously developing. Artists are recognized through gallery and museum exhibitions, as well as through auctions, but what many fail to observe is that artists are being acknowledged through the fashion industry as well. Although there are several collaborations that have already been extensively researched and analyzed, there are countless others that need the same scholarly attention. Through the process of research and interviews, both artists and designers are studied and questioned in regards to their participation within the collaboration. The case studies included analyze the benefits and outcomes of the brand alliance between designers and artists.