In dealing with complex and ill-defined systems of an offshore application, modelling of human reasoning for the purpose of risk assessment requires the effectiveness of a systematic logic-based approach. Floating production, storage and offloading (FPSO) installations, for example, combine traditional process technology with marine technology, and thus are quite dependent on technical design and operational safety control. Such safety-critical dependencies require novel approaches to properly analyse the risk involved. Hence, a proposed framework utilising approximate reasoning and evidential reasoning approaches is provided for modelling the assessment task. As based on fuzzy set theory, the model enables uncertainties to be described mathematically and further processed in the analysis of the structures. The forms of membership functions that could be used in representing fuzzy linguistic variables to quantify risk levels are presented. A case study of collision risk between FPSO and shuttle tanker due to technical failure during tandem offloading operation is used in this paper to illustrate the application of the proposed model. Furthermore, the obtained results from the case study provide confirmation that at various stages of offshore engineering systems design process the framework of incorporated approximate reasoning is a suited and convenient tool for attaining reliable risk analysis.