Introduction. In the present-day scientific discourse, there is a great number of theoretical research focusing on the problem of objectifying the semiotic nature of law and analysing the functional construct of legal semantics. Whereas, many practical legal issues, such as: interpretative ambiguity in the meaning-formation and meaning-application of normative acts, lexical vagueness and contextual dependence of legal notions and the incoherence of legal terminology across different legal systems, remain neglected, which leads to contradictions and inaccuracies in legal practice. The aim of the study is to define the methodological principles fostering establishment of the acceptable scope of semantic interpretation of legal notions in the context of building a legal thinking culture. Materials and Methods. The research methodology was based on the principle of jurisprudential definition of legal norm meaning-formation in socio-legal discourse. Analytical, systematizing and pragmatic methods were used to reveal a complex nature of the semantics of law in the context of legal thinking development. The semiotic analysis of the objectivity and normativity of legal notions taking into account the contextual differences of legal definitions, was used as a specialised research method. Results. It was established that normative notions are the complex semantic constructs encompassing a conceptual sphere (normativity) and social reality. For building sustainable models of legal behaviour and legal culture, it is necessary to overcome external and internal conflicts in interpretation of law. In this regard, a number of advisory measures were proposed aimed at establishing acceptable scope of semantic interpretation: differentiation between the informational nature of prescriptive and descriptive notions, semantic monitoring of legal phenomena, and implementation of the principle of discourse contextualism, which makes it possible to formulate the normativity of law requirements based on the specific contextual interpretations. Discussion and Conclusion. A justified conclusion about possibility of a properly selected semantic toolkit to determine the objectivity of perception of the legal norms and, consequently, to improve the process of building a legal culture was drawn. The main advantage of the principle of discourse contextualism such as conjunction of the semantics and pragmatics of legal notions was identified, which provides a fruitful foundation for further theorizing on the nature and metaphysics of law.