Taddeo di Bartolo was born in Siena. The exact year of his birth is unknown, but it’s been suspected to be between 1363-65. He was the son of a certain Bartolo di Maestro Mino, a barber, and not of the painter Bartolo di Fredi, as Vasari believed, and therefore not the brother of Andrea di Bartolo. Around 1389 he entered the Sienese Guild of artists, where he mastered the art of painting among his Sienese colleagues. In 1389 Taddeo traveled to Collegarli, the San Miniato al Tedesco hills, and Pisa. The painting of "The Virgin and Child Enthroned", signed and dated in 1390 and created in the church of San Paolo in Pisa, is one of Taddeo’s first documented works. In 1393, Taddeo traveled to San Gimignano, where he executed the altarpiece of the "Virgin and Child and Saints" (1395) for the Sardi and Campigli Chapel in San Francesco. The "Virgin and Child With Saints" showcases Taddeo’s earlier style. The thin, elegant figures, and flowing lines of the drapery patterns reflect influence from his Sienese predecessors, such as Simone Martini and Ambrogio Lorenzetti.