Readers of Diogo Bernardes’s (ca. 1530–ca. 1595) poetry have long praised the brandura (gentleness) of his work. But what brandura meant and how favorably it was viewed depended on context. Brandura was associated with the middle style, with mastery of elocutio, and, by extension, with poetry’s ability to move those who listened to or read it. Therefore it could at one moment provoke moral anxiety and at another signal the height of poetic accomplishment. In quarrels over the relative merits of the European vernaculars, apologists for the Portuguese language invested in Bernardes’s reputation as brando (gentle), as he was said to demonstrate the brandura of their mother tongue. Yet later in the seventeenth century his fortunes sank. Though he is little esteemed today, his association with the multiple meanings of brando and brandura implicated him in important political, moral, and aesthetic disputes throughout the sixteenth and seventeenth centuries. By paying renewed attention to style and affect in the context of cultural history, this essay aims to revive interest in Bernardes’s work.