Pole assignment is a basic design method for synthesis of feedback control systems. In this paper, a gradient flow approach is presented for robust pole assignment in synthesizing output feedback control systems. The proposed approach is shown to be capable of synthesizing linear output feedback control systems via on-line robust pole assignment. Convergence of the gradient flow can be guaranteed. Moreover, with appropriate design parameters the gradient flow converges exponentially to an optimal solution to the robust pole assignment problem and the closed-loop control system based on the gradient flow is globally exponentially stable. These desired properties make it possible to apply the proposed approach to slowly time-varying linear control systems. Simulation results are shown to demonstrate the effectiveness and advantages of the proposed approach.