In this text, Spanish chairs from the 16th century are studied – “sillas de brazos” /chairs with arms – with upholstery in decorated leather. This article begins with the history of the owners and their family connections with inland Portugal, and the arrival of these chairs to Oporto, in the turbulent years of the early 20th century. The authors resort to family history, and studies of furniture from both Iberian countries. Leather upholstery receives a detailed study, both in the decorative technique (patterned tooling and carved leather) and in its setting in the Renaissance in Spain; these chairs are placed in parallel with Portuguese pieces of the same epoch (the “cadeiras d’espaldas”/chairs with back), revealing the considerable differences in the art of leather carving, both in aesthetics and in technique.