The study of Early Modern Iberian footwear is taking its first steps. Both historiography and archaeological research have devoted little attention to this issue and organic remains found in excavation even tend to be discarded. This paper will address the results of DRESS project’s questioning about courtly footwear, whose research benefited from a multidisciplinary team that included archaeologists familiar with the assemblages from which it was still possible to recover remains for analysis. The data provided and analysed starts with the study of the footwear evidence found in the Angra D shipwreck (Azores), a 16th century site. However, we soon noticed that this isolated study did not comprehensively provide information on the subject and two other intertidal archaeological sites were added: assemblages from Santa Clara-a-Velha (Poor Clares) Monastery in Coimbra (late 16th and 17th century), situated on the south bank of the Mondego River, and archaeological remains from the Campo das Cebolas (Old Market), on Lisbon waterfront (16th–17th century). Data from three archaeological sites were collected, drawn, and analysed, and a comparative methodology was applied. In the absence of syntheses for Iberian world, we used both critical bibliographies pertaining to North European collections and visual parallels, resulting on the first typological series of Iberian footwear.