Dental modification represents one interesting aspect of corporeal adornment in human history that directly reflects personal social identity. Tooth filing choices distinguished certain individuals at the urban, Maya political capital of Mayapan from 1150 to 1450 ad, along with cranial modification, nose and ear piercings, tattoos and body paint. Here we examine how filing teeth, considered a beautification practice for women at Spanish Contact in the sixteenth century, is distributed across a skeletal sample of males, females, elites and commoners in this city. We evaluate the normative claim of the Colonial period and determine that while predominantly females filed their teeth, most women chose not to. Sculptural art further reveals that male personages associated with the city's feathered serpent priesthood exhibited filed teeth, and we explore the symbolic meaning of filed tooth shape. Assessing the practice in terms of associated archaeological contexts, chronology and bone chemistry reveals that it did not correlate with social class, dietary differences, or birthplace. Residents of Mayapan, a densely inhabited, multi-ethnic city of 20,000, engaged with multiple material expressions of belonging to intersecting imagined communities that crosscut competing influences of polity, city, hometown and family scale identity. Tooth filing reflects identities at the individual or family scale.