: The aim of this study was to gain an understanding of the element playfulness in fashion photographs related to openness and multiple significance in contemporary art. A total of 105 fashion photographs from US and UK Vogue magazine editorials and advertisements for the last five years were selected for the study. The photographs were analyzed in two main categories -the contextual element of themes, and the elements of visual expression; composition, models, objects and editing technology. The element of playfulness in the photographs were found to be divided into themes of infantile fantasy, social satire and situational dissonance, and elements of visual expression were found to express image distortion, expansion, exaggeration, reduction, and optical illusions. A photography type termed as infantile fantasy and social satire have descriptive characteristics and usually deliver the message by using models and objects to present a certain situation or express social satirical viewpoint and reflective attitude by using objects and photographic skills. A photography type termed as situational dissonance is characterized by immediately understood expressions and usually clarify the message by using a photographic technology such as editing the printed image or expect the model to express an exaggerated poses and ridiculous expressions, causing an optical illusion. Visually expressed and composed scene using composition, models, objects and editing technology is a specific character of photograph and due to the advances in computer editing technology it has been able to express the various playfulness.