This study is to analyze fashion phenomenon according to the concept of the characteristics of freewheeling to explain the de-constructive, eclectic, avant-garde tendencies in Contemporary Fashion. This study is to elicit the aesthetic characteristics through 400 pieces of visual data analysis from 2001S/S to 2011F/W that have the characteristics of freewheeling, nontechnical experiments do away with the classical form. The oriental ideas include the thoughts of different tastes that break the stereotypes according to the Western values and the pursuit of unconventional beauty. These also insist that everything in the world including human-being, nature and creation is not divided into two equal parts, and even beauty and ugliness originated from one. This study is to find the possibility of interpreting oriental aesthetics with open concepts that transcends the boundaries of full availability, unlike the Western values that accommodate the relative concept of the pursuit of diversity. Therefore, integrated and systematic approaches of oriental aesthetics that place much value on the coexistence of antithetic concepts are needed to understand the ambiguity of complexity and diversity in Contemporary fashion design.