Simulacre means a copy of the original, an ostensible representation of someone or something. This study closely looks at the 2017 <VOGUE like a painting exhibition> hosted by the fashion magazine Vogue. The purpose of this study is to use both theoretical and empirical analysis to analyze the simulacre developed in fashion photographs inspired by famous paintings in the exhibition booklet. The booklet is divided into four sections: portrait, rococo, landscape painting, from avant-garde to pop art. It also contains 55 pieces comparing the original masterpieces to the works of 26 photographers inspired by them. The fashion photographs were analyzed using Jean Baudrillard’s four stages of simulacre transformation: represent, denature, dissimulate, and replace image change theory. The degree of simulacre expression was indicated three times on a four-point Likert scale by five fashion majors, and the results were integrated and analyzed. As a result, in fashion photography, simulacre— due to the development of photography technology and the photographer’s artistry— appeared in various ways; image denature was most preferred, followed by dissimulate, represent, and replace. This study shows that image analysis of fashion photographs and applying the perspective of simulacre when creating artworks can be a way to obtain rich qualitative data in the future.