Florida’s approach to urban and regional development focusing on innovation and the creative class spurred an awareness of how space and particularly soft locational characteristics are related to economic performance. In the light of two decades of theoretical discussions and empirical findings, this chapter reflects on three aspects of Florida’s creative class approach. First, the definition and measurement of the creative class, second, the role of contextual differences for the outcome of the relations that are argued in the approach, and third, a discussion of what has changed in the last 20 years since Florida launched his book and to what extent the arguments are valid today with a specific reference to Europe.