During endurance exercise, skin temperature (Tsk) plays a fundamental role in thermoregulatory processes. Environmental temperature is the biggest determinant of the Tsk. During exercise, the response of the skin temperature might be influenced by aerobic fitness (VO2peak). The aim of this study was to analyze and compare the dynamic of Tsk in high (HF) and moderately (MF) fit endurance runners during a progressive maximal stress test. Seventy-nine male endurance runners were classified into HF (n = 35; VO2peak = 56.62 ± 4.31 mL/kg/min) and MF (n = 44; VO2peak = 47.86 ± 5.29 mL/kg/min) groups. Tsk and cardiovascular data were continuously monitored during an incremental exercise, followed by a recovery period of five minutes. Results revealed that the MF group exhibited lower VO2peak, Speedpeak, ventilation (VE), muscle mass %, and higher BMI and fat mass % than the HF group (all p < 0.001). HF had significantly higher Tsk at baseline, and at 60% and 70% of peak workload (all p < 0.05). Tskpeak correlated with age, fat mass %, muscle mass %, VO2peak, Speedpeak, HR and VE (all p < 0.05). These findings indicate that VO2peak was positively associated with increased Tsk during incremental exercise in male endurance runners.