[2] One of his earliest documented works is the painting of The Virgin and Child Enthroned, signed and dated in 1390, executed in the church of San Paolo in Pisa.
The thin, elegant figures, and flowing lines of the drapery patterns reflect influence from his Sienese predecessors, such as Simone Martini and Ambrogio Lorenzetti.
[3] Around 1401, Taddeo painted in Duomo di Santa Maria Assunta in Montepulciano the celebrated altarpiece, The Assumption of the Virgin and scenes from The Passion of Christ.
[4] In 1403, Taddeo produced two works in Perugia, now on display in the public gallery there: the Virgin and Child with two Angels and St Bernard and the Descent of the Holy Spirit.
Many of his new paintings represent the Life of the Madonna, including the Death of the Virgin in which Jesus descends, takes her hand, and receives her in the form of an infant.