The advent of various arts and remarkable development of mass media since 1980s accelerate fashion photographs' advancement. The expression of fashion through photographs can represent characteristics of ages, societies, cultures, traits of designers and techniques of photographers. This study focuses on Cindy Sherman's fashion photographs, which represent different kinds of respect to the women's states and identity. Cindy Sherman describes neglected women, sexual characteristics, and tries to overcome the limitation existing in modern society. By analyzing her fashion photographs, women's identities can be examined and the new trial of fashion photographs' expression is able to be considered as well. The results are summarized into two traits. The first is grotesque images, which have strange cuts, dissolved and deformed bodies. Those are expressions to subvert the stereotype of women. The second is amusement, which is expressed with uncanny and ridiculous appearances. These fun images are challenges to depict human instinct and also symbolic plays.