Stylistic fronting (SF) is an optional syntactic phenomenon whereby a lexical item that may belong to various syntactic categories fronts to a pre-finite-V position, if no subject is merged in SpecIP. The literature reports that SF is productive in Icelandic and Old Scandinavian, and it is also attested in some Old Romance languages (Old Catalan, Old French). This article presents a phase-based analysis of SF in Old Italian. In this language, SF has some previously undiscussed characteristics. A corpus study shows that Old Italian displays a root/nonroot asymmetry in the typology of fronting items. In root clauses, nominal elements, such as nominal predicates with a special semantics, front more frequently than verbal elements (infinitives, past participles), which most frequently front in nonroot clauses. Since fronting in root clauses is intrinsically ambiguous with topicalization and focalization, it is not considered SF and is not extensively discussed in this article. By contrast, I analyze as proper SF the fronting operation that occurs in nonroot clauses, and I argue that this is a movement anchoring the event-structure (vP) semantic content to the context (FinP). This type of movement is possible only if vP is not a phase and no intervening agentive external argument is merged in SpecvP. The fronted material is pragmatically presupposed and interpreted as the subject of predication. Pragmatics tests corroborate the argument.