Protective and sport clothing is governed by protection requirements, performance, and comfort of the user. The comfort and impact performance of protective and sport clothing are typically subjectively measured, and this is a multifactorial and dynamic process. The aim of this review paper is to review the contemporary methodologies and approaches for measuring ergonomic wear comfort, including objective and subjective techniques. Special emphasis is given to the discussion of different methods, such as objective techniques, subjective techniques, and a combination of techniques, as well as a new biomechanical approach called modeling of skin. Literature indicates that there are four main techniques to measure wear comfort: subjective evaluation, objective measurements, a combination of subjective and objective techniques, and computer modeling of human–textile interaction. In objective measurement methods, the repeatability of results is excellent, and quantified results are obtained, but in some cases, such quantified results are quite different from the real perception of human comfort. Studies indicate that subjective analysis of comfort is less reliable than objective analysis because human subjects vary among themselves. Therefore, it can be concluded that a combination of objective and subjective measuring techniques could be the valid approach to model the comfort of textile materials.