Gas insulated transmission lines (GILs) are being used in electrical systems regarding power transmission and substation interconnection. However, operational complexities of conventional schemes, such as structural rigidity, corrosion protection, gas leakage in case of seismic vibrations, larger bending radius and jointing complexities which restrain their application perspectives, could be curtailed by developing a flexible GIL. In this research paper, a new pliable scheme of gas insulated transmission line is proposed. Further, COMSOL Multiphysics® (version 5.1, COMSOL Inc., Stockholm, Sweden) based electrostatic assay and practically performed high voltage tests-based dielectric analysis is performed for the proposed scheme. Electrostatic appraisal is comprised of field utilization based electrostatic stress analysis. In addition, dimensional optimization of pliable GIL regarding enclosure and pitch sizes in relation to electrostatic stresses and field utilization is also performed. Regarding dielectric perusal, experimental setup has been developed for standard lightning impulse and disruptive discharge tests in order to investigate the synergistic dielectric characteristics of proposed flexible post insulators for pliable GIL. Experimental and simulation appraisal unveil that the proposed scheme exhibits almost analogous electrostatic and dielectric behavior in comparison to the conventional GIL scheme and could simplify the operational intricacies associated with conventional scheme. The proposed modifications could eliminate the requirement of trench development, corrosion protection and acceleration dampers, along with a significant reduction in required land area at bends, due to a smaller bending radius which will ultimately result in substantial cost reduction.