It has long been argued that Byzantine iconophile theology had as a natural corrolary an intense devotion to the humanity of Christ. This can be seen in the writings of Theodore the Studite (759–826), for whom a proper understanding of, and devotion to, Christ’s humanity was the linchpin of the whole debate. It carried over, moreover, into his distinctly earthy or “incarnational” approach to sanctity, in which the mundane tasks of the coenobitic monastery were extolled in some detail as comprehensive paths to holiness. The link between Theodore’s doctrinal commitments as iconophile and his role as monastic theorist and reformer is briefly examined in the first part of this paper. The second part turns to a specific question arising from Theodore’s interest in the humanity of Christ that concerns the status of Christ’s human nature. Cholij briefly discusses a passage in which Theodore speaks of Christ assuming a human nature that has been corrupted/spoiled (φθαρεῖσαν) by sin, explaining the phraseology as an outcome of his passionate iconophile stance. Taking Cholij’s suggestion forward, a fuller analysis of Christ’s humanity and its soteriological import in Theodore will be offered. Firstly, it will be argued that Theodore’s approach cannot be forced into debates regarding Christ’s human nature as “fallen” or “unfallen.” Secondly, however, it will be contended that Theodore’s theological concern for the humanity of Christ is a foundational marker for more developed notions on this theme such as those offered by Symeon the New Theologian, himself a disciple of Studite monasticism.