When moving, children very often see the city from a window view. Best-selling children’s books and popular cartoons also show cars as the norm for how we move around. In this car-oriented infrastructure and imaginary, it is difficult to think about other, healthier options. The idea of a social imaginary connects various fields of study, from psychology to architecture, and is the matrix of innovation and change. But how can someone nudge the imaginary into being a more sustainable one? This is where Radical Children’s Literature may come in handy. The concept first appeared to describe books published between 1910 and 1949 across Europe and North America. Writers saw children’s books as a way to challenge dominant norms and to create the social will necessary for remodeling society within people of all ages. From a Radical Children’s Literature perspective, the discussion can start from an early age and show that the world's structure is not inevitable. In this sense, books that shift the parameter for urban design and focus on how children experience the city can be one of the first steps to create new urban imaginaries and develop urban literacy. We need more stories that engage readers in debates about socio-spatial inequalities, promote cycling and walking as a way to move and explore the surrounding environment. Stories that inspire activism and stories in which children have agency on the streets.