This preliminary study investigates cognitive complexity, or an individual’s cognitive structure for his or her social world, and its role in stylistic innovation, particularly changes of design in the appearance or symbolic meaning of products, for five Taiwanese small design firms. The results reveal that cognitive complexity is useful to understand the stylistic innovation processes of Taiwanese entrepreneur-designers. The entrepreneur-designers use cognitive complexity to determine the structural prerequisites of aesthetic products. The domain-specific cognitive complexity of the entrepreneur-designer influences the selection of relevant and appropriate dimensions in stylistic innovation. Entrepreneur-designers’ strategic decisions to target a customer-oriented market or designer-driven market will affect the selection of stylistic orchestration and agile synchronization in the process of stylistic innovation.