The city of Herculaneum offers an exceptional analytical laboratory for the study of decorative elements in domestic environments and a reading of images in their architectural contexts. This paper is focused on the case of insula V at Herculaneum, which was a truly mixed habitat (class/families). The analysis of the paintings in context is approached on several scales (insula, house, room, wall) throughout the dwelling, in order to provide a diachronic analysis of the decoration. As I shall demonstrate, the houses were modified several times in response to the changing needs of the occupants, to accommodate different activities (economic activities, in particular) or to accommodate additional inhabitants (i. e., newly-married sons, freed slaves who were granted an apartment). These renovations to the ground floor could be combined with the addition of an upper level (where one could move, for example, the living quarters of the proprietor). What were the consequences of these architectural transformations on the decoration of the dwellings? What aesthetic choices were made to include old decoration in the new decor of the renovated houses?