The aim of this essay is to examine how Stockholm has been portrayed in paintings and postcards during the last 500 years. In this essay my research material is collected mostly from literature about the subject matter. The pictures of paintings and postcards are analyzed with a semiotic picture analysis method to discover similarities and differences in how they have been depicted. The goal of the study is to find both common and divergent elements in the images that can place them in a historical context and mediate something about the century they were made in. The study has concluded that there are several similarities and differences in how images of Stockholm has been depicted during the centuries that I have been studying. In both paintings and postcards there has been recurrent elements such as the water surrounding Stockholm, and the way the mediums have been beautifying the city to highlight some characteristics. A striking difference during the centuries is the usage of people in the images.