Paul’s exhortation in 1 Cor 11:2–16, discussing (among other topics) the reason and purpose for a woman to cover her head, has proven to be a perennially difficult passage for exegetes. Cynthia Long Westfall has recently offered an intriguing interpretation, asserting that some modern, Western readings of the passage, which view Paul’s directives as reinforcing oppressive restrictions on women, fail to account for the way the veil acted to protect certain vulnerable women from potential exploitation. Westfall asserts that many women of the Greco-Roman world, especially of the lower strata, would have seen veiling as a desirable symbol of dignity, though socially and legally unavailable to them as members of repressed social groups. In this study, the authors test Westfall’s dual assertion that (1) veiling practices varied significantly depending on one’s social strata and that (2) authorities legally enforced veiling restrictions on certain groups. Ultimately, although the article supports aspects of Westfall’s argument, the authors find no evidence to uphold the assertion that veiling was off-limits for any female group in the Greco-Roman world. Rather, an array of sociocultural factors—including religious expectations, societal norms, and practical realities—appears primarily to have influenced a woman’s choice to veil.