Gripping comfort evaluation was crucial for designing a product with good gripping comfort. In this study, a novel evaluation method using gripping posture image was constructed based on convolutional neural network (CNN). Human subject experiment was conducted to acquire gripping comfort scores and gripping posture images while gripping seven objects with simple shape and eleven manufactured products. The scores and the images were used as training set and validation set for CNN. Classification problem was employed to classify gripping posture images as comfort or discomfort. As a result, accuracies were 91.4% for simple shape objects and 76.2% for manufactured products. Regression problem was utilized to predict gripping comfort scores from gripping posture images while gripping cylindrical object. Gripping posture images of radial and dorsal sides in direction of hand were used to investigate effect of direction of hand on prediction accuracy. Consequently, mean absolute errors (MAE) of gripping comfort scores were 0.132 for radial side and 0.157 for dorsal side in direction of hand. In both problems, the results indicated that these evaluation methods were useful to evaluate gripping comfort. The evaluation methods help designers to evaluate products and enhance gripping comfort.