In the context of the retail business, rarely studied the impact of top transformation leaders on middle management personnel creativity. In this study, the middle management personnel of 258 retail enterprises were discussed, explored the impact of top transformation leaders on the double-dimensional creativity of middle management personnel, and analyzed individual psychological security. Results show that transformational leadership (morale modeling, visionary motivation, individualized consideration, and charisma) has a significant positive impact on the progressive creativity and breakthrough creativity of middle managers. Transformational leadership (Same as the above four dimensions) has a significant positive impact on the psychological security of middle managers. Psychological security has a significant positive impact on the progressive creativity and breakthrough creativity of middle managers. Psychological security plays a partially mediating role between transformational leadership and the creativity of middle managers. Among which, it plays a partially mediating role between morale modeling and progressive creativity, visionary motivation and progressive creativity, individualized consideration and progressive creativity, charisma and progressive creativity, morale modeling and breakthrough creativity, and charisma and breakthrough creativity, while it plays a fully mediating role between visionary motivation and breakthrough creativity, individualized consideration and breakthrough creativity. This study expanded the study of psychological security as an intermediary variable and deepened the study of dual-dimensional creativity. Based on the above conclusions, this paper puts forward relevant suggestions to promote the development of progressive creativity and breakthrough creativity of middle-level managers, to provide a reference for enterprises to maintain talent advantages and for managers to enhance development potential.