Sustainable urban planning promotes a mixed use of crossroads by pedestrians and vehicles, regulating traffic flow and improving street's liveability. Design of pedestrians' underpasses, reduction of street's width by physical barriers and, more generally, walkability limitations may reduce liveability of any urban place, stimulating wrong pedestrians' behaviours. The present study explores the linkage between urban design, micro-scale landscape quality and the underlying socioeconomic local context in Valie Asr crossroad, one of the most important cultural and commercial centres in Tehran, Iran. By investigating pedestrians' perceptions and public orientation toward urban liveability in Valie Asr, this contribution provides a reflection on urban planning, informing design of attractive and comfortable streets for pedestrians considering urban liveability. Results of a field survey assessing behaviours of the pedestrians and the overall landscape quality of the place provide practical indications to improve urban design based on sustainability principles, with the final objective to make public spaces more attractive for residents and visitors