After attending the celebrations of Catherine of Aragon’s 1501 arrival in London, Thomas More referred to her retinue as “barefoot pygmies from Ethiopia,” revealing how Catherine and her retinue were seen by some as threateningly alien even as other citizens described her as “faire.” My argument considers this mixed perception in light of an earlier debate between Catherine’s parents, Ferdinand and Isabella of Spain, and her future parents-in-law, Henry VII and Elizabeth of York, over the extent to which Catherine ought to be “Englished.” Turning to under-consulted letters housed in Simancas, Spain, I consider how these discussions over the extent to which Catherine should be stripped of her Spanish identity were eventually complemented by Catherine’s subtle “Spanishing” of the English court. This bleeding of Spanishness into the English cultural landscape reflects the necessarily hybrid identity of all foreign queens consort—educated to advocate for their birth nation while living in a country that expects them to adopt their ways. Catherine’s eventual success as an influential queen consort reflects how she learned to present herself as non-threateningly English even as the residue of Spanishness in her dress reflects her quiet, behind-the-scenes work on behalf of Spanish interests.