The orders of architecture remain a prominent feature in the study of European architectural history, often presented as a universal system of mathematical proportion. Yet, when looking into the column theory devised by Wittkower and tracing it to Renaissance authors as Leon Battista Alberti and Sebastiano Serlio, a more complex system of mathematical interpretation culminates. The column theory applied architectural orders as either pillars or columns in walls, yet they contain design principles for elongating the proportion of architectural orders based on their position in walls. Based on this principle, the early modern architect interplayed with the perception of edifices through proportional deviation and mathematical play. Hence, this chapter proposes a conjoint reading of Alberti’s De re aedificatoria (1485), Serlio’s Regole generali (1537), and Wittkower’s Architectural Principles to reformulate how design principles culminated and allowed for local appropriations of Renaissance architecture through mathematics.