Significance attributed to the principle of equality in contemporary constitutional democracies of the national, supranational (EU) and international level (UN, CoE) is self-evident. Some of the most significant moral crusades in history have been fought and won in the name of “equality”: abolishment of slavery, elimination of feudal privilege, the spread of universal suffrage, the outlawing of racial discrimination, the emancipation of women, etc. The mere word “equality” has quite a powerful and persuasive rhetorical force not only because of what it refers to but also due to its very nature. It combines two paradoxical features: although it appears to have universal meaning, it seems to mean different things to different people. It is not the intention of this paper to analyse the equality principle in abstract terms, but rather to discuss the constitutional order of Italy, primarily through relevant constitutional case-law. The first chapter is an overview of the Italian constitutional framework within which the equality principle operates. The second part is dedicated to the case law of the Constitutional Court of the Republic of Italy from its beginnings until today. A special emphasis is given to the principle of reasonableness, the use of comparators, and the limits to the Court’s adjudication. The third part looks in detail at the relationship between paragraphs 1 and 2 of Article 3 of the Italian Constitution, i.e., the relationship between the concepts of formal and substantive equality. Special attention is paid to affirmative action programmes and particular interpretative techniques developed in the context of the concept of substantive equality. Both the wording of the Italian Constitution and the Constitutional Court’s interpretation disclose a belief that equality never stands alone as an abstract concept; instead it should be put in the full context of life, pursuing an understanding of what it means to be a full and flourishing person. The specific equality provisions of the Constitution point to the critical areas in the Italian society: the position of women, language minorities and inter-religious relations.