This study was intended to analyze and investigate a diversity of aesthetic values expressed in the military look of the Milan collections by using content analysis method to find what design characteristic and image emerged concretely in the later 20th century. A total of 334 military look works shown in fashion magazines such as Vogue and Collezioni Donna over the period between 1996 and 2000 were collected as research data, which were classified into 5 categories such as item, silhouette, color, color coordination, fashion image. The results were summarized as follows: first, it was found that coat was the most preferred item in expressing the military look image. Second, it was found that the straight line was the most preferred silhouette, which indicates that it was the most suitable silhouette in expressing the bisexual image of the military look. Third, in the colors of the military look, achromatic colors such as black and white were found to be of the highest frequency, which shows that achromatic colors continued to be proposed as fashionable colors around 1996 and this influence was reflected in the military look. Finally, in terms of the item of color coordination, monochromatic coordination accounted for more than half of the military look, through which it could be explained that designers utilized it greatly to make an effective expression of the masculine image.