The chopine, one of the most extraordinary forms of footwear ever worn in Western dress, was integral to the sartorial splendor of upper-class women's dress throughout southern Europe in the fifteenth, sixteenth and early seventeenth centuries. However, this early modern fashion did not represent a single monolithic style; different regions produced distinctly different forms of chopines and they were worn in strikingly different ways that were framed by local issues related to gender construction, familial prestige, civic identity and the promotion of the industries that drove local economies. This essay traces the history of the chopine from antiquity to its dissemination across the Iberian Peninsula under Roman rule and then its transformation by the Moors into an unrivaled feature of upper-class women's dress in both Christian Spain and Italy. A detailed comparison between the late sixteenth-century luxury tapins of Valencia and the exceptionally high calcagnetti of Venice illuminates the regional difference in the ways in which chopines were made, how they were worn and how they came to be a paramount accessory of women's dress in Spain and Italy. The essay also addresses hybridism evidenced in some Italian chopines and chopines as a trans-Mediterranean fashion.