This paper aims to monitor brand image of two important fashion cities on social media (Instagram). Through a content analysis of pictures and texts authors attempt to identify the main associations that various actors have of London and Florence, both traditionally strictly related to the fashion system. As recent literature has argued for brands or products, even for places and cities (Gilboa et al. 2015), it is important to monitor the perceived city brand image resulting from the overall online experience (Choi et al. 2007), especially on social media. Indeed, it is demonstrated that word of mouth on social media is able to strongly affect users’ perceptions (Gretzel, Yuan, and Fosenmaier, 2000), thus contributing at the construction of the city brand image. This paper is one of the first one that applies content analysis on Instagram in city/place branding, where the core of communication is based on images. Therefore, differently from previous studies (Andéhn et al. 2014; De Moya and Jain, 2013), this work principally focuses on visual communication, as form of textual paralanguage communication (Luangrath, Peck, and Barger, 2016), for the construction of city image of London and Florence.