Daily working activities and functions require a high contribution of hand and forearm muscles in executing grip force. To study the effects of wearing different gloves on grip strength, under a variety of hand skin temperatures, an assessment of the maximum grip strength was performed with 32 healthy male workers with a mean age (standard deviation) of 30.44 (5.35) years wearing five industrial gloves at three hand skin temperatures. Their ages and anthropometric characteristics including body mass index (BMI), hand length, hand width, hand depth, hand palm, and wrist circumference were measured. The hand was exposed to different bath temperatures (5 °C, 25 °C, and 45 °C) and hand grip strength was measured using a Jamar hydraulic hand dynamometer with and without wearing the gloves (chemical protection glove, rubber insulating glove, anti-vibration impact glove, cotton yarn knitted glove, and RY-WG002 working glove). The data were analyzed using the Shapiro–Wilk test, Pearson correlation coefficient, Tukey test, and analysis of variance (ANOVA) of the within-subject design analysis. The results showed that wearing gloves significantly affected the maximum grip strength. Wearing the RY-WG002 working glove produced a greater reduction on the maximum grip when compared with the bare hand, while low temperatures (5 °C) had a significant influence on grip when compared to medium (25 °C) and high (45 °C) hand skin temperatures. In addition, participants felt more discomfort in both environmental extreme conditions. Furthermore, they reported more discomfort while wearing neoprene, rubber, and RY-WG002 working gloves.