Traditionally, the presence of the shadow economy (SE) has been associated, mainly and positively, with taxation. Recently, some authors have suggested that the SE may be also linked to the institutional setting (efficiency of the bureaucracy, regulations, corruption, etc.) so that just two stable equilibria are possible. In the “good” one, there is a small hidden sector, large fiscal revenues and honest/appreciated institutions. The other, “bad”, equilibrium is the opposite. Unlike the traditional approach, therefore, the recent literature argues that the tax burden and SE can be negatively correlated. Examining the links between these variables in relatively uncorrupt systems, this paper reconciles the two views. Theoretically, it claims that many different good equilibria can emerge whereby SE and its determinants are linked in complex and different ways. For instance, taxation and SE can go hand-in-hand, even taking into account the institutional framework. Empirical evidence for OECD countries supports both the model and the changing nature of the SE.