Sustainability, while being definitely a new form of humanity, as it has been proposed and dealt with in many urban and landscape projects, lacks often of an essential characteristic of the anthropic space: seduction. The authors believe that sustainability has to find its own power of seduction if it is to compete successfully with the ambiguous but established charms of the unsustainable city. From all the above it is clear that the importance of the ‘aesthetic of sustainability’ is fundamental for the success of a new model of green planning not just from an environmental and economic point of view, but, perhaps and most importantly, from a social and mental one. This paper will investigate the possibility to look at sustainability and aesthetics through the lens of evolutive processes and the complexity theory to inform a new Bottom-Up/Self-Organized approach as a possible morphogenetic process for sustainable city design. Often criticized as the theory of ‘out of control’ the complexity theory applied to the urban could instead be the enabler of a new paradigm where the notion of single authorship with intellectual ownership and his aesthetic language is substituted by the concept of a collective and a new aesthetics of choice where aesthetics might recover, according to the evolutionary theory, their essence of an ‘adaptive system’ and an ecological category.