By addressing two separate branding exercises for Amman, Jordan, we investigate the links between the city’s image and the visual image of its brand. We build on previous research by proposing a theoretical framework that combines city branding, Canter’s theory of place and Kevin Lynch’s Image of the City. We test this theoretical framework by contrasting the development of Amman’s city brand in 2002 and its rebranding exercise in 2009. We address, first, how Amman’s brand(s) and image(s) are linked, and second, how the city brand and its image influence and are influenced by the values Ammanis ascribe to their city. We find that while it incorporated intensive promotional campaigns and place-making interventions, the 2002 branding exercise excluded the residents of Amman; the ensuing brand image therefore failed to correspond to the residents’ perceived values of Amman. Conversely, Amman’s 2009 branding exercise aspired for an inclusive process (‘inward branding’), which allowed the new brand and its ensuing image to be ‘lived’ by and to ‘enliven’ Ammanis. We thus trace how Amman’s 2009 branding effort achieved more success among residents than the multidimensional branding exercise of 2002 simply by capturing the intricacies between residents’ affective perceptions and the new brand image.