Obesity is a disease of civilization. The COVID-19 pandemic has caused an increase in its incidence; therefore, there is an increasing emphasis on programs aimed at improving body composition, often through physical activity. Various modifications to training interventions are being introduced, including the modification of the thermo-climatic conditions of the training. However, to date, whether such a modification is safe for the skin has not been studied. The purpose of this study was to evaluate the effects of a series of workouts in a hypoxic chamber on skin characteristics such as elasticity, hydration, and transepidermal water loss (TEWL). Women who were overweight or obese were invited to participate in the project. The workouts took place in a hypoxic chamber where conditions were mimicked at 2500 m, three times a week for a period of four weeks, for 60 min each. Finally, the results from 11 women in the study group and 9 in the control group were included in the analysis. Body composition analysis was performed, and venous blood was drawn (morphology and lipidogram). No statistically significant changes in skin firmness or the amount of TEWL were observed in the subjects. An increase in skin hydration on the hand was observed only after the first workout (p = 0.046), while skin hydration on the mandible did not change. A significant reduction in body weight (p = 0.042), BMI (p = 0.045), and TBW (p = 0.017) was indicated in the study group. The control group showed an increase in BMI (p = 0.045) and VFA (p = 0.042). There was no correlation between measured skin characteristics and body composition indices or the results of blood indices. A correlation was observed between TEWL and lipidogram results. Training under hypoxic conditions does not affect skin features in overweight and obese women. Even a significant reduction in TBW did not result in a decrease in hydration. It was also shown that the proper barrier function of the skin is closely dependent on the serum lipid profile.