Issey Miyake is one of the most innovative fashion designers, today. His “Pleats Please” clothing line is well known in the fashion world. The Miyake’s design style is an exhibit of simplicity, creativity, and practicality. He escaped from following the fashion trend and re-searched for the origin of clothing’s vitality. Through his explorations of the relationship between the body and its coverings, dressing becomes a fun, poetic, and humorous behavior. Issey Miyake’s works seem intangible, but sparse and not dispersed. It is this mysterious oriental culture’s expression that gives the magical charm of his works. This study uses a case study method, gathers references, and applies the theory of Habitual Domains to analyze the rich habitual thinking of Issey Miyake. This research identifies that core empowering operators for Issey Miyake’s design philosophy and success are treating everyone as a priceless living entity; understanding there are reasons for everything that occurs; and having the enthusiasm and confidence to accomplish mission. The source of his inspiration and creativity was influenced mostly by internal factors and least by external factors. Issey Miyake understood that deep down and voids principle. Utilizing the meditation to illustrate vivid forms of image, he developed the perfect example of the integration of culture and fashion. The unique and creative design led by him is far beyond the boundary of "time" and "fashion". He was able to take full advantage of habitual domains to nurture mind and body, and to enrich human behavior. He thus became a charismatic mater of fashion design and philosophy, that is worthy for younger generation to follow.