This paper presents the measurement results of the thermal insulation of the outer shell, thermal inserts, and clothing systems, as well as a comparative analysis of the thermal insulation of multi-layer thermal inserts in a thermal jacket intended for professional services in cold weather. Detachable thermal inserts are made of double-faced, diamond-shaped quilted lining with different masses per unit area, and together with the jacket, they form clothing systems with different thermal properties. Tests of the thermal properties of clothing were performed on a thermal manikin. They showed that an increase in the mass of thermal insulation textile materials contributes to an increase in the thermal insulation properties of clothing and are insufficient for a complete analysis of the thermal properties of clothing. Therefore, for the first time, three new parameters of integration efficiency of the thermal insert, thermal insulation efficiency parameters, and efficiency parameters of the integration of the textile material integrated into the clothing system were introduced. Based on these parameters, it is possible to perform an effective and accurate comparative analysis of the thermal insulation of multi-layer thermal inserts in clothing. This makes it possible to apply exact scientific methods largely in the technical design of the thermal properties of integrated textile materials, instead of experience-based methods as in the past.