Like many urban spaces in the Global South, Brazilian cities are renowned for their extreme inequalities, with socio-spatial distinctions generally following a center/ periphery divide in which wealth and infrastructure are concentrated in center districts, and social vulnerability increases the farther out one goes. Yet, in the past fifteen years, poverty reduction, planning initiatives, higher education opportunities, and social media networks have transformed many urban periphery communities and residents' aspirations for the future. In this article, I explore some
of the visions of what city life in São Paulo is and might be. I begin with an overview of São Paulo's spatial landscape and the polysemic category "the periphery." I then turn to two differently scaled examinations of intentional spatial and cultural transformation in São Paulo's Zona Sul (southern zone). The first is a study through reflection of local sustainable development policy in two environmentally protected areas, the second an autoethnographic-inflected exploration of the growth in recent years of what I call insurgent cosmopolitan periphery subjectivities. My analysis considers how center-led public policies and periphery-based cultural movements, may, in different ways, simultaneously re-enforce existing social segregation and support the creation of new spatial possibilities, space-based subjectivities, and life ways in urban landscapes.