The study aims to investigate the concept of Smart Sustainable Cities in traditionally planned and organically grown settlements. Smart Cities Mission is an ambitious project of Government of India targeting 100 cities for improving their urban quality of life. However, there is no universally accepted definition of smart cities because of its vast and vague scope. In such a situation, it becomes important to understand where our old cities stand in terms of smart sustainability and inclusiveness. The methodological approach adopts case analysis of old Indian cities and Arab cities in terms of their environmental, economic and social planning paradigms. These include land use mix, compact development, dwelling density, internal and external connectivity, open spaces, walkable neighbourhoods, access to social services, collective cohesiveness, local area governance, crime & safety, economic diversification and socio-cultural diversity. The study enlists smart urban elements in our existing old cities, which are derived from extensive literature study of Middle East cities and primary surveys of around 160 samples in a medium sized old Indian city in Rajasthan. The study assesses the baseline situation of culturally rich and varied old cities and need to advance from their inherent smartness using innovative and interactive ICT and urban engineering solutions.