Critical theorizations of Naples are widely cited in philosophy, cultural studies and urban studies, as well as in cultural representations of the city. Such theorizations have generated a series of images and discourses that—no less than their literary, cinematic or artistic equivalents—have shaped cultural understandings of the city but without being subject to the same level of critical enquiry. This article analyses the corpus of critical theorizations of Naples from the 1920s and the 1990s-2000s. Deploying a postcolonial approach, it identifies in Benjamin and Lacis’ influential theorization of Neapolitan “porosity” the operation of a “northern/Orientalist gaze” that constructs the city as other to “a certain Europe [conceived] as the primary habitus of the modern” (Chakrabarty). It further assesses the relative success of subsequent theoretical attempts to evade the pitfalls of porosity and to approach and understand Naples on its own terms.