Dressed in a crisp white ruff and paned red velvet doublet, the young man – long thought to be a depiction of the artist himself – twirls his brush on his palette, as if about to begin a composition on the stretched canvas just out of view. This portrait exemplifies Lorenzo Lippi’s interest in naturalistic, clearly defined forms. Lippi began his career in the workshop of Matteo Rosselli, who recognized his talent for what Francesco Baldinucci called his 'sola imitazione del vero,' or 'singular imitation of truth' (F. Baldinucci, Notizie dei Professori del Disegno da Cimabue in qua, V, Florence, 1847, p. 262). While Lippi's early independent works are closely related to his master’s style in their attention to the soft, rich folds of drapery, facial types and delicate sfumato, the present painting represents a shift toward a more precise handling of light and shadow, a hallmark of his mature works.

Mina Gregori dates this painting to around 1639, by which point Lippi had already left Rosselli’s studio, enrolled in the Accademia del Disegno and established his own workshop (loc. cit.). Lippi’s circle included poets, writers and the painters Francesco Furini, Cesare Dandini, Salvator Rosa and Bartolomeo Bimbi, all of whom influenced his late style. While long considered a self-portrait, Gregori posits that this portrait may instead represent one of Lippi’s students, executed before he took up a post as court painter to Claudia de Medici (1604-1648) in Innsbruck in the early 1640s (loc. cit.). Given the relatively early date of the painting and the sitter's apparent age, it is perhaps likelier that he was a peer of the artist rather than a pupil.