The article focuses on the central plaza of the city of Samarqand, the seat of Transoxiana under the Sogdians and again under the Timurids. The earliest edifice on the Rigestān square is an early fifteenth-century madrasa named after the Timurid prince-scholar Ulugh Beg. Although the capital was transferred to Bukhara after the final conquest of Samarqand by the Uzbeks in 1500, the Shaibanids and their successors, the Ashtarkhanids, continued to embellish Samarqand with more imperial constructions. The Rigestān thus received its final form with two additional madrasas, the Shirdār and the Talākāri, by 1660. The article aims at describing and evaluating these structures and their architectural details, vis-à-vis the latest scholarship on art history.