For contemporary planning, the notion of streets as support for everyday urban life has been absent. Since the surge of the private car as the predominant mode of mobilityMobility, the street has been losing complexity; its uses have been oversimplified. It has merely become the means to go from A to B in the fastest possible way. Transportation in the city has been reduced to artificial engines, putting aside walking and cycling as basic and essential means of mobilityMobility. Against the prevailing principles of modern urban planning, we think that any discussion about the city should first and foremost consider people—especially those who, because of their age or gender, historically did not have access to automobiles. The imaginary of the patriarchal society has positioned men in the public and exterior realms while women were in static, invisible, and interior places. However, the realities experienced by many women have been neither homogeneous nor binary-simplistic, the masculine exterior versus the feminine interior. In reality, working women have always been on the street and walked to their places of work, even though those public and labor spaces were not planned for them. As we witness the end of the automobile era, this chapter argues for the need to recuperate Jane Jacobs’s thinking, who claimed for diversityDiversity of life on the street while introducing urbanismUrbanism from a gender perspective. As case studies, we are considering developments in two European cities: Vienna, which in response to the demands of feminist movements has been incorporating gender perspectives in urban planning for more than thirty years; and Barcelona, which echoing Vienna’s example, is introducing design proposals and policies towards evolving into a more equitable city for all.