Born, Giovanni di Jacopo di Guido da Caversaccio, in Lombardy, Milano became active in Florence, painting for the city’s Churches. His painting was true to the times, influenced by Giotto di Bondone, the Great Giotto (1267 – 1337), a style many artists in Florence followed at the time. His works also show an influence from the Sienese painter, Simone Martini (1280 – 1344).
His first fully attributed work was the polyptych of Madonna and Saints for the Prato Spedale della Misericordia. His Ognissanti Polyptych depicting several saints, now hangs in the Uffizi Gallery. He also painted frescos depicting the Life of the Virgin and the Life of Mary Magdalene, in the Rinuccini Chapel of the Basilica di Santa Croce di Firenze. One of his last works executed was the Man of Sorrows, but there is also record that he was commissioned in 1369 by Pope Urban V (1310 – 1370), collaborating with his fellow Florentine, Giottino (1324 – 1369) in Rome.