Practicing in accordance with the principle of Naturalness (Zìrán) is an idea present in all schools of Taijiquan (Tai Chi Chuan). Zìrán has its origins in cultural developments in ancient China. The ideas that make up Zìrán are recorded in Lǎozi's Classic of the Way and Virtue (Dàodé Jīng), the central book of the Taoist tradition, and have been disseminated in martial arts and self-cultivation practices over the past 2,500 years. Zìrán is a state of balance and stability. Imbalance would affect both the world and the human being, who are part of the same continuum. This worldview would influence many later developments, such as Taoism, around the 2nd century. Together with self-cultivation and divination practices, Taoism took deep root in China by introducing ideas that were simple, practical, and discussed to this day. These concepts permeate Chinese culture, including therapeutic body practices and martial arts practices - which later became different styles of wǔshù, especially the so-called internal schools (nèi jiā). The objective of this study is, therefore, to understand what Zìrán is according to historical records and the confluences of this classical thought with its representations in recent times, through statements by contemporary Tàijí quán instructors in documentary sources and digital media. The selected speeches are attributed to four nationally and internationally renowned Tàijí quán masters who have published books on the subject. The sources were analyzed in light of Cultural History and underwent Content Analysis for better interpretation of the prospected data. The Dàodé Jīng presents five occurrences of mentions and explanations of Zìrán. There are also countless mentions of Zìrán in the documents, as the ideal way to practice in alignment with the Dào. Likewise, we find, in the masters’ statements, an emphasis on seeking to carry out training in a state of balance and naturalness. We even identify what Zìrán would be in relation to combat tactics, represented in detail by the “intrinsic energies” practiced in tuīshǒu. In this case, we perceive a form of combat tactics quite distinct from that present in the most popular martial arts. We realize that the principle of Zìrán is present in the imagination of different generations of Tàijí quán practitioners, shaping training according to representations originating from cultural formulations that are thousands of years old. This is not only clear evidence of the processes of rationalization and ritualization of fighting practices, but also evidence of the appropriation and presence of elements of Taoism in martial arts. Understanding these processes can greatly assist the teaching of Chinese martial arts, avoiding distortions and the emptying of meanings of the historicity of these practices.