Friction has been the most widely exploited anti-loosening (AL) mechanism. The threaded fasteners are desired to have predictable frictional torques (Tf) values and minimum stress concentration. The goal of this study is to assess the available fasteners in terms of the abovementioned criteria to choose the most optimal design. We categorized frictional fasteners into five types according to the torques generation mechanism. For each group, we made and examined both an experimental specimen and a 3D finite element method (FEM) model. Results show that only the fastener type, in which Tf are generated by the radial force, satisfies the criteria. Developing frictional fasteners of such type can be a promising future research direction. Additionally, the study gives some recommendations on the AL performance evaluation.