The Pitti crystal column, preserved at the Uffizi Museum, is one of the most refined glyptic objects of the Renaissance age. Owing to its decorative system on a miniature scale, the significance of many of its scenes has remained unclear, and hence, as a consequence, so have its function, iconological message, the meaning of its all'antica style, and its intended recipient. Using detailed images of each engraved scene, this paper shows how the decorative system of the artefact (originally a mirror) is related to King Philip II of Spain (1527–1598). The entire decoration was designed to eulogize Philip II, and especially the Battle of Saint-Quentin (1557), and his consequent control over some Italian lands (Milan, Naples, Sicily and Sardinia) after the Treaty of Cateau-Cambrésis (1559). The paper investigates the reasons why Trajan's Column was chosen as an inspirational model for the Pitti column and how such an ancient model was re-elaborated and renewed through the combination of other elements that came from a wider antiquarian all'antica repertoire. In this way, it is possible to show that this valuable artefact is a clear example of how the use of all'antica style in the Renaissance was not purely referencing a glorious past, but was adapted to the use of the object itself.