Since the 1980s, different conceptions of regionalism have emerged, reflecting distinct perspectives on place and space and a variety of policy orientations. The debates in planning over which regional policies are both “equitable” and “democratic” have been intense. This article clarifies these debates through a critical regionalist approach to the two prominent “regionalisms,” investment and distributive. This article then proposes how to strengthen the connections between investment and distributive regionalism and build on the successful practices in each arena. The authors argue that a progressive regionalism requires focus on (1) the labor market as a whole and (2) multiscalar coalitions and policy initiatives.