The effect of the thermal properties of steels on wire drawing behavior has been investigated to understand and improve the wire drawing process. Finite element analysis and experimental tests were conducted to analyze the temperature distribution of the deformed specimens with different thermal properties. The thermal properties of twinning-induced plasticity (TWIP) steel were measured and compared with those of plain carbon steel. Based on the measurement of thermal properties, wire drawing behaviors were systematically compared with thermal conductivity of the specimen (k) using plain low-carbon steel with high k and TWIP steel with low k. The results revealed that the k of TWIP steel was approximately one third of that of low-carbon steel, and the thermal expansion coefficient of the TWIP steel was approximately 50% higher than that of low-carbon steel in the temperature range of 26–400 °C. The temperature distributions in the wire strongly depended on the k of the wire during wire drawing. TWIP steel exhibited higher maximum temperature, and took a longer time to attain the equilibrium temperature than low-carbon steel during wire drawing owing to the low k. The maximum temperature of the die increased with decreasing k of the wire, indicating that die wear can increase with decreasing k of the wire. Therefore, reducing the drawing speed is suggested for a wire with low k, such as high-alloyed metals, especially for TWIP steels.