The contra-sexual phenomenon that is recently focused is one of the new factors, which is focused when explaining the life style of progressive woman’s image and it is creating cultural category. Moreover, the contra sexual people that are rising as new consuming subjects are not simple primary consumers but their shopping culture and cultural tastes are giving effects to many people. Because of the tendency, marketer of consuming industry are making efforts to predict the changes of contra-sexual people’s shopping habits and tastes. Therefore, it is necessary to grasp contra-sexual phenomenon and research the fashion design aiming at that in order to predict woman’s fashion image in the future. Therefore, the study considered concept and characteristic of contra-sexual phenomenon and surveyed its example in the popular culture. And, the study analyzed the formative characteristic of contra-sexual fashion shown in the public cultures such as drama and movie. On the basis of the result, design was suggested by reflecting contra-sexual fashion characteristic under the concept of ‘Urban Splendor’. From the results above, it was possible to grasp the concept and characteristic of contra-sexual phenomenon, which appeared as a trend and understand new woman’s image and the fashion that has changed because of it. It is considered that the establishment of the foundation of contra-sexual phenomenon, which plays as an important variable in woman’s fashion, fashion accessory, cosmetic and advertisement field but it is hard to clarify, by analyzing the work aiming at contra-sexual phenomenon will be helpful for predicting the change of woman’s fashion in the future.