Background: Trail running socks with the same fibers and design but with different separations of their three-dimensional waves could have different thermoregulatory effects. Therefore, the objective of this study was to evaluate the temperatures reflected on the sole of the foot after a mountain race with the use of two models of socks with different wave separations. Material and Methods: In a sample of 34 subjects (twenty-seven men and seven women), the plantar temperature was analyzed with the thermal imaging camera Flir E60bx® (Flir systems, Wilsonville, OR, USA) before and after running 14 km in mountainous terrain at a hot temperature of 27 °C. Each group of 17 runners ran with a different model of separation between the waves of the tissue (2 mm versus 1 mm). After conducting the post-exercise thermographic analysis, a Likert-type survey was conducted to evaluate the physiological characteristics of both types of socks. Results: There was a significant increase in temperature in all areas of interest (p < 0.001) after a 14 km running distance with the two models of socks. The hallux zone increased in temperature the most after the race, with temperatures of 8.19 ± 3.1 °C and 7.46 ± 2.1 °C for the AWC 2.2 and AWC 3, respectively. However, no significant differences in temperature increases were found in any of the areas analyzed between the two groups. Runners perceived significant differences in thermal sensation between AWC 2.2 socks with 4.41 ± 0.62 points and AWC 3 with 3.76 ± 1.03 points (p = 0.034). Conclusion: Both models had a similar thermoregulatory effect on the soles of the feet, so they can be used interchangeably in short-distance mountain races. The perceived sensation of increased thermal comfort does not correspond to the temperature data.