Abstract: Robert Herrick's central oxymoronic trope in Hesperides (1648) of diligent negligence has traditionally been understood in general aesthetic terms. This essay argues that this trope, particularly as evoked in the poem "Delight in Disorder," relates especially to the art of rhetoric and that it had special currency in the language of curiosity deployed in the rhetorical discourse of the period, especially in the area of preaching. The essay begins by situating Herrick's poem in relation to contemporary rhetorical thought distilled, from Cicero via Justus Lipsius, in John Hoskyns's Directions for Speech and Style and expressed in the sartorial metaphor of Herrick's poem. It then turns to contemporary homiletic discourse to tie these ideas into the language of curiosity as applied to questions of arrangement ( dispositio )—the central concern in the poem's examination of appeal in female "dress"—arguing that it is this rich rhetorical context that provides the energeia of Herrick's poem.