The goal of this research, contorted from the perspective of media aesthetics, is to uncover the ways how mechanical/cybersensual fashion products express aesthetic characteristics of cybernetics, by comparing them with digital products designed by an application of cybernetics. The other goal is to provide a cultural and design framework of cybernetics as d digital-environmental medium for fashion in which hightech and human sensibilities are fused. The results urged to explore two new contrasting perceptual possibilities for an understanding of digital technology application: negative and positive feedbacks. Cybernetic optimism, centered on technological dimensions, focuses on a concept of fashion that emphasize instrumental aspects-efficiency and convenience. In contrast, cybernetic pessimism focuses on digital fashion that expresses environmental destruction and the loss of human identity. A comparative analysis of the aesthetics of expression in digital fashion design and digital industrial products from a cybernetic perspective showed that in digital environment society, the combination of negative and positive feedbacks resulted in design products in which internal and external aspects of beauty complemented each other.