The estimation of the value of goods belonging to the different categories of ‘conspicuous consumption’ could be rendered complex for various factors, such as the heterogeneity of the goods and their quality, or the changes in taste and style in view of models of social distinction. With reference to fifteenth-century Lombardy, this chapter considers the moment of estimation and its values (legal, economic, moral and social), and takes account of some significant categories of luxury goods such as jewelleries and pieces of clothing, handwritten and printed books, antique objects and artwork. The aim is to analyse some peculiarities of the evaluation procedures and identify the most important changes occurred over time. This results in establishing who the persons and which expertise procedures were best suitable for evaluating the different types of goods.