This study examines two religious paintings created during the European Renaissance – Francesco di Giorgio Martini’s The Nativity (circa 1460–1465) and Luca Signorelli’s The Birth of St. Nicholas of Bari (circa 1500–1520) – focusing on their deviation from the naturalistic depictions characteristic of the period. The anomalous composition and elements present in these paintings likely stem from the practical and economic context behind their creation. Both works contain inconsistent perspectives, improper anatomy, unusual color choices, and distorted spatial arrangements. These irregularities are especially striking given that both artists demonstrated high levels of technical mastery in their other contemporary works, making The Nativity and The Birth of St. Nicholas of Bari appear stylistically regressive in comparison with Martini and Signorelli’s other paintings created around the same time. While some inconsistencies can be justified and interpreted as enhancing the meaning of the paintings, this analysis contends that such distortions in composition are not merely signs of limited skill or deliberate stylistic devices. Instead, they represent compromises that allowed the artists to produce accessible religious imagery tailored for modest, private worship. Due to the fiscal constraints of a non-elite commissioner, the artists may have intentionally sacrificed formal precision to emphasize critical elements and prioritize a clear religious narrative. This study thus explores how economic limitations shaped artistic choices, resulting in works that diverge from Renaissance norms while fulfilling devotional functions.