The paper is devoted to Nikolay Lossky who was one of the leading Russian philosophers of the first half of the twentieth century. We demonstrate the interrelationship between three aspects of Lossky’s philosophy: realism in the theory of knowledge, hierarchical personalism, and supra-naturalistic concept of evolution. We pay attention to the contemporary relevance of Lossky, and we discuss and critique his ideas in light of those of other philosophers. Lossky acknowledges that the subject interacts with being itself and that knowledge is not a shadow or copy of being. His ontology is based on intuitivism and epistemological optimism. Its main categories are God, as the super-systematic principle, and monads. In Lossky’s metaphysics, the idea of abstract ideal principles of being is quite harmoniously combined with personalism. Lossky’s ontology has strong ethical underpinnings. He considers that values are rooted in being and that the evolution of the world is directed by God towards the good. Lossky elaborates a supra-naturalistic concept of evolution. He extrapolates principles of teleological determination, which are fundamental to human existence, on the underlying levels of the world as a whole. Many trends of modern thought are in tune with Lossky’s philosophy, including a return to metaphysics, panpsychism, Platonism, and the desire to unite the religious worldview with new scientific discoveries.