Abstract Islamic modesty as a cluster of gendered virtues is typically synonymous with ‘modest’ modes of body-concealing attire and comportment. This article argues, however, that the meaning of ‘modesty’ as currently conceptualised to illuminate the contours of corporeal and sartorial piety is wholly inadequate in its inability to evaluate the more ambivalent expressions of modesty beyond dress as a signal of inner virtue. Although the attention on modest or pious fashion as embraced by women the world over has been as a site for redefining the boundaries of moral and public participation, it does not go far enough in reconfiguring the debates on aesthetics and ethics of ambivalence, ambiguity, and contradiction in Muslim society. Based on a textual reading of the public persona of the Malaysian celebrity entrepreneur Dato Vida and interviews with other Malay-Muslim female entrepreneurs of her contemporary, I posit that the elasticity of modesty relates to a similarly flexible, expansive, and explorative conceptualisation of Islam. Related to this conceptualisation, Dato Vida embodies what I call ludic piety in her presentation and performance of gendered pious excesses within the elastic bounds of modesty.