Gentile (di Niccolò di Massio) da Fabriano was born around 1370 in or near Fabriano, in the Marche. Despite having several family members who took part in different civic and religious organizations in the city, much of Gentile's early life remains undocumented. His mother died some point before 1380, and his father, Niccolò di Giovanni Massi, retired to a monastery in the same year, where he later died in 1385. Little is known of his educational formation: one of his first known works, a Madonna and Child (c. 1395–1400, now in Berlin) shows the influence of paintings made in the northern Italian late-Gothic style. Around 1390 Pavia resided at the court of Gian Galeazzo Visconti, where there is a table with the Madonna with the Children together with the saints Clara and Francis (now in the Pavia Civic Museums) and some frescoes depicting ladies inside a room of the Visconti Castle.
By around 1405, Gentile da Fabriano was working in Venice. He painted a panel for the church of Santa Sofia, now lost; Jacopo Bellini worked perhaps in his workshop. Between 1408 and 1409, he painted a fresco (now lost) in the Doge's Palace depicting the naval battle between the Venetians and Otto III. In Venice, he knew Pisanello and perhaps Michelino da Besozzo. He also produced commissions for other cities during this period, such as his Madonna and Child (c.1405-1410) for a church in Perugia.

In 1410–1411, Gentile was in Foligno, where he frescoed some of the walls of the Palazzo Trinci. Gentile met painter Michelino da Besozzo in Venice and became inspired by his rhythmic and sophisticated style. Around 1410–1412, he painted one of his first masterworks, the Valle Romita Polyptych (now at the Pinacoteca di Brera). The altarpiece was probably commissioned by Chiavello Chiavelli upon its completion in 1412. In 1414, he moved to Brescia, at the service of Pandolfo III Malatesta, and painted the Broletto Chapel, a work now mostly lost, for the next five years. While in Brescia in 1418, Gentile painted another panel that was later given as a gift to Pope Martin V, who had passed through the city on his way to Rome.

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