[2] Giorgio Vasari, the first art historian of the Renaissance, writes in his Lives of the Artists that Lippi was inspired to become a painter by watching Masaccio at work in the Carmine church.

Lippi's early work, notably the Tarquinia Madonna (Galleria Nazionale, Rome) shows the influence of Masaccio.

[7] Louis Gillet, writing for the Catholic Encyclopedia, considers this account and other details reported about Lippi, as "assuredly nothing but a romance".

[2] With Lippi's return to Florence in 1432, his paintings had become popular, warranting the support of the Medici family, who commissioned the Annunciation and the Seven Saints.

Cosimo de' Medici had to imprison him in order to compel him to work, and even then the painter escaped by a rope made of his sheets.

One of these, placed to the right, is a half-length figure originally thought to be a self-portrait of Lippi, pointed out by the inscription is perfecit opus upon an angel's scroll.

[citation needed] This relationship resulted in their son Filippino Lippi in 1457, who became a famous painter following his father,[6] as well as a daughter, Alessandra, in 1465.

In 1457, he was appointed commendatory Rector (Rettore commendatario) of San Quirico [it] in Legnaia, from which institutions he occasionally made considerable profits.

This series, which is not wholly equal to the one at Prato, was completed after Lippi's death by assistants under his fellow Carmelite, Fra Diamante.

[6] The frescoes in the choir of the cathedral of Prato, which depict the stories of Saint Stephen and Saint John the Baptist on the two main facing walls, are considered Fra Filippo's most important and monumental works, particularly the figure of Salome dancing, which has clear affinities with later works by Sandro Botticelli, his pupil, and Filippino Lippi, his son, as well as the scene showing the ceremonial mourning over Stephen's corpse.

His principal altarpiece in this city is a Nativity in the refectory of San Domenico: the Christ child on the ground adored by the Virgin and Joseph, between Saints George and Dominic, in a rocky landscape, with the shepherds playing and six angels in the sky.

[10] A group of bystanders depicted at the funeral includes a self-portrait of Lippi and his helpers, Fra Diamante and Pier Matteo d'Amelia, together with his son Filippino.