The fashion market within Singapore is gaining prominence. At the same time, its rapid development has led to volatility being present within the Singaporean fashion-retail marketplace. C+C&Co is a collaborative Singapore-based Southeast Asian creative company which was established in 2011. As an entity that is part of the creative services sector, C+C&Co’s multidisciplinary core competencies of image making, branding, and design consultancy creates a full-suite solution for local brands. The nature of the work produced alongside other industry collaborators creates an environment where collaborators are both clients and partners at the same time. This case evaluates client interviews conducted by C+C&Co with Singaporean designers Reckless Erika, Pauline Ning, Ling Wu, and Gnome & Bow to demonstrate the issues that local designers, such as these, experience within the fashion market in Singapore. This information will itself expand on the benefits and limitations of a collaborative work structure and will help to guide students in determining the areas where business problems can manifest in the fashion market within Singapore. The case proposes that a collaborative work structure is useful in identifying the ongoing challenges whilst also suggesting that the adaptive nature of the structure is beneficial for brands’ changing needs. By the end of this case study, students will be able to suggest improved and more effective collaborative work structures.