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This article examines the controversial fashion of veiling in the early modern Spanish world. Working across the media of art, literature, and the law, it explores the intersecting ways in which moralists, legislators, playwrights, painters, and poets constructed the figure of the veiled lady (tapada) as a social type at once alluring and deeply unsettling. We provide an explanation of the terminology and taxonomy of veiling, with illustrations to show the various styles of face-covering popular in early modern Spain. We then argue that this fashion and the controversy—as well as the entertainment—it generated were closely tied to Spain’s rise as an imperial power, especially to the new forms of urbanism that developed in the ancient city of Seville and the much younger capitals of Madrid and Lima. As these rapidly expanding cities offered their inhabitants new spaces of social interaction and new possibilities for social mobility, wealth, and consumerism, their changing urban landscapes and complex demographics also generated anxieties of failure and deception. Cultural concerns regarding religious practice, the regulation of domestic and public space, and racial and class distinctions coalesced around the figure of the tapada. Seductive, mysterious, and rebellious, she absorbed the fantasies and fears of urban life in three of the most dynamic cities of imperial Spain.