This article attempts to use different ways of looking that help classroom and visual art teachers analyze the meanings attributed to visual images, thereby enhancing their visual literacy skills. In the study, holistic multiple-case sampling was employed in the context of case study method as each group of teachers was individually considered as an analysis unit and their analysis of visual images through different ways of looking was evaluated in a holistic way. The participants of the study comprised of a total of 508 teachers who attended teacher training workshop of the Project titled 'The Implementation of Visual Culture Theory on Primary and Secondary Visual Arts Courses.' The data were collected with worksheets, artistic drawings and participant diaries and analyzed inductively. The data were presented in three themes: analyzing visual elements, approaching the visual contextually, and determining the contributions of visual experience. The results denoted that classroom and visual arts teachers interacted with images through a series of questions related to different ways of looking at visual images, questioned visual representations, artistic components and sub-meanings and created various meanings in terms of social, economic, psychological and cultural contexts, thereby increasing their visual literacy skills.