Window displays in the fashion industry are unique sites of meaning that combine advertising and artwork in a three-dimensional space. The current body of research surrounding window displays approaches the subject from a marketer’s position and attempts to evaluate performance. This project shifts the focus to the artistic qualities of window displays as they are used by fashion retailers. The primary theoretical lens is gestalt theory, which has applications in both psychology and design. The specific windows examined are the Christmas windows at retailer Saks Fifth Avenue Toronto in December of 2018. An autoethnographic research design is employed, resulting in an exploratory empirical analysis that serves as an entry into an under-represented area of study: the fashion window as an art object. The key findings of the project are the application of gestalt theory to the design of the windows and the researcher’s observations to suggest an explanation of the public’s response to the displays.