Despite its indisputable fame, the "Made in Italy" style—whose design is notoriously an important feature—does not correspond to a strongly regulated quality brand. In the last decades, this gap has been filled by the creation of a set of public and private institutions shaping and defining what "Made in Italy" is. One of the most prestigious of these institutional devices is the Compasso d'Oro Award, established in 1954 by La Rinascente department store and then managed by the Italian Designers Association. Since its birth, an Executive Committee composed by designers, architects, entrepreneurs, and academic scholars ran the Compasso d'Oro and contributed to its organization, creating a strong connection between design and industry. In most of thirty editions from 1954 to 2008, the Compasso d'Oro selected 24,000 items and awarded more then 2,000 products and enterprises. The wide range of actors and activities involved in the award makes it an interesting observatory to analyze the design system's evolution in Italy in the last sixty years. In this paper, we will observe this evolution in two ways: by a quantitative analysis of items, enterprises, and designers honored by the prize, and by a qualitative analysis of the criteria of its attribution set up by the Jury from 1954 to the present. Through this combined investigation, we will show that in the course of time the Compasso d'Oro and other organizations (such as Triennale and Salone del Mobile) have built a "conventional set" of informal rules able to specify and enforce the Italian Design's image and reputation despite the lack of the "Made in Italy" system's regulation by public authorities.