Previous studies of the influence of structural qualities of urban street network on the image of the city are based mainly on centrality and connectivity measures taken from graph and space syntax theories. The paper suggests application of the structural property of eccentricity for considering the structural distinctiveness or differentiation of a given street in the overall street network. Eccentricity suggested by Q-analysis and based on the perspective of multidimensional chains of connectivity. This structural property is applied to the case of the city of Tel Aviv by using a geographic database of the street network and observed data acquired from Tel Aviv residents’ production of sketch maps. The study’s findings provide preliminary evidence for the relevance of the structural property of eccentricity for understanding the relationships between street network and the image of the city.