The paper focuses on the interlacement of literary and iconographic elements by displaying an innovatory philological and stylistic approach, from a comparative perspective, in thematizing multilingual translational and adaptive aspects, ranging across Bernard Berenson's diaristic and epistolary corpus, in conjunction with his works on Italian visual culture. This interweaving gives occasion to the elaboration of multilinguistic textual influences and their verbo-visual artistic representations deduced from his innovative interpretative readings in the domain of world literature in modern times. Such analysis of the discourse of theoretical and literary nature, and of the pictoricity, refers to Bernard Berenson's multilingual considerations about canonical authors in English, Italian, French, German language, belonging to the Neoclassical and Romantic period, as well as to the contemporary era, as conceptualized in his autobiographical works, in correlation with his writings on Italian figurative art. The scope of this presentation is to discern and articulate Berenson's aesthetic ideas evoking literary and artistic modernity, that are infused with crucial notions of translational theory and conveyed through the methodology of close reading and comprising at the same time, in an omnicomprehensive manner, a plurality of tendencies intrinsic to social paradigms of cultural studies. Unexplored premises reflecting Berenson's vision of Italian culture, most notably of a visual stamp, will be analyzed through author's understandings of such adaptive translations or volumes to be subsequently translated in Italian, and through their intertwined intertextual applications, significantly contributing to further critical and hermeneutic reception thereof. Particular attention is drawn to its instancing in the field of Romantic literary production (Emerson, Byron), originally underscoring the specificities of each literary genre and expressive mode, of the narrative, lyric or theatrical nature, as well as concomitantly involving parallel notions as adapted variants within visual arts, and in such a way expressing theoretical views pertainable to Italian artworks too. Other analogous elements relevant to literary expression in the most varied cultural sectors such as philosophy, music, civilisational history (Goethe, Hegel, Kant, Wagner, Chateaubriand, Rousseau, Mme de Staël, Taine) are furnished, as well as the examples of the resonances of non-western cultures, with the objective of exploring the effect among readership bringing also to the renewal of Italian tradition.