This study investigated how cognitive style and training context influenced visual discrimination skill acquisition and transfer under time pressure. This experiment consisted of a screening session, a training session, and a transfer session using random polygon comparison tasks. Screening session was designed to separate participants according to their cognitive style (analytic or holistic). Training session was divided into difficult and easy conditions. In transfer session, participants compared polygon pairs in a novel task. The stimuli were presented for 1.5 seconds to examine the influence of time pressure. Through the all sessions, this experiment measured accuracy and response time. According to the results of this study, analytic group responded as quickly as holistic group in the beginning of training session because time pressure induced them to the holistic strategy. However, as training session progressed, their slopes of reaction time increased, suggesting that their own analytic style emerged. Holistic group showed flatter slopes than did analytic group for training session. Of interest is the slopes increased at the beginning of transfer session, suggesting that they developed analytic strategies in difficult training context. It is suggested individuals differently develop strategic processing skills depending on cognitive styles even under time pressure.