unregulated spaces

Sennet keeps returning to the need for ambiguity in urban environments . He seems to be responding to the over design of certain modern buildings and streets that do not allow for an evolution or interaction developed over time with use, that do not accomodate adaptations. But also that we  need more, not less, challenging spaces. Guy De Bord coined the phrase psychogeography in a response to the perception that everyday life is controlled and manipulated by over regulation. Are there examples of actual places and spaces that respond to these ideas?