In 1931 Lauterpacht described the Italian scholarship as characterized by a ‘rigid and frequently uncompromising positivist school in international law’. While his statement has some merits, this chapter seeks both to illustrate how this trend emerged from previous approaches and, conversely, to emphasize the multifaceted perspectives that were effectively present in those decades, thus partly circumscribing Lauterpacht’s assertion. Following a survey of the fluid approaches present at the beginning of the twentieth century, this chapter will introduce the pivotal role of Dionisio Anzilotti in favoring legal positivism, even if dissident voices were still present or subsequently emerged. After Anzilotti, other poles of attraction emerged, in particular through Santi Romano and other scholars, who, while still claiming to adhere to the lines of positive law, deprived this conception of several of its original theoretical attributes. Conversely, few attempts were made to elaborate doctrines aimed at reflecting the political ambitions of Fascism, which was unsuccessful in influencing the broad theoretical debate.