Oil–paper insulation is the critical insulation element in the modern power system. Under a harsh operating environment, oil–paper insulation will deteriorate gradually, resulting in electrical accidents. Thus, it is important to evaluate and monitor the insulation state of oil–paper insulation. Firstly, this paper introduces the geometric structure and physical components of oil–paper insulation and shows the main reasons and forms of oil–paper insulation’s degradation. Then, this paper reviews the existing condition assessment techniques for oil–paper insulation, such as the dissolved gas ratio analysis, aging kinetic model, cellulose–water adsorption isotherm, oil–paper moisture balance curve, and dielectric response technique. Additionally, the advantages and limitations of the above condition assessment techniques are discussed. In particular, this paper highlights the dielectric response technique and introduces its evaluation principle in detail: (1) collecting the dielectric response data, (2) extracting the feature parameters from the collected dielectric response data, and (3) establishing the condition assessment models based on the extracted feature parameters and the machine learning techniques. Finally, two full potential studies are proposed, which research hotspots’ oil–paper insulation and the electrical–chemical joint evaluation technique. In summary, this paper concludes the principles, advantages and limitation of the existing condition assessment techniques for oil–paper insulation, and we put forward two potential research avenues.