The Vitruvian Man—originally known as “The proportions of the human body according to Vitruvius,” the celebrated Roman architect and writer known for the only treatise on architecture to survive from antiquity—presents the divinely based geometric proportions of the human body as the underlying structure that binds architecture to the divine order of the world. The Vitruvian Man, a drawing by the famous Renaissance painter and thinker Leonardo da Vinci that demonstrates a male figure in two superimposed positions with arms and legs apart and simultaneously inscribed in a circle and a square, can be compared to the premodern Sufi master Ibn ‘Arabi’s Universal/Perfect Man (al-Insan al-Kamil) as represented in his Insha’ al-Dawa’r (Creating/Constructing Circles) and al-Futuhat al-Makkiyya (The Meccan Openings/Revelation). In circular and square diagrams in these treatises, Ibn ‘Arabi presents his mystical view of the divine geocentric cosmos, the domains of being, and the place and role of the human being. In a multilayered spherical world, the Universal Man exists at the middle of the sphere of fixed stars, the innermost circle, like a pillar (‘amd) holding up the ceiling of the sky. Using cross-disciplinary methodologies of art history and mystical studies, this paper articulates this comparison as a means to grasp the profound difference between Eastern and Western cultures. Why was the circle in connection with the square an ideal diagrammatic representation of the world? How were these representations manifested in architecture thinking and practice in premodern times and now? This paper attempts to answer these key questions drawing on both primary and secondary sources. Although Ibn ‘Arabi’s diagrammatic non-figurative circles have been discussed extensively, a comparison with the figurative Vitruvian Man has been overlooked despite its significance. This comparison provides insight into the artistic and religious anthropomorphic representation in the Western and the Islamic civilizations throughout classical antiquity, premodern Islam, and the Renaissance, with reflections on the modern representation and manifestation of the circle beyond architecture.