Flutter-driven triboelectric nanogenerator (FTENG) is one of the most promising methods to harvest small-scale wind energy. Wind causes self-fluttering motion of a flag in the FTENG to generate electricity by contact electrification. A lot of studies have been conducted to enhance the energy output by increasing the surface charge density of the flag, but only a few researches tried to increase the converting efficiency by enlarging the flapping motion. In this study, we show that by simply replacing the rigid flagpole in the FTENG with a flexible flagpole, the energy conversion efficiency is augmented and the energy output is enhanced. It is found that when the flag flutters, the flagpole also undergoes aerodynamic force. The lift force generated from the fluttering flag applies a periodic rotational moment on the flagpole, and causes the flagpole to vibrate. The vibration of the flagpole, in turn amplifies the flutter of the flag. Both the fluttering dynamics of the flags with rigid and flexible flagpoles have been recorded by a high-speed camera. When the flag was held by a flexible flagpole, the fluttering amplitude and the contact area between the flag and electrode plates were increased. The energy enhancement increased as the flow velocity increased and the enhancement can be 113 times when the wind velocity is 10 m/s. The thickness of the flagpole was investigated. An optimal output of open-circuit voltage reaching 1128 V (peak-to-peak value) or 312.40 V (RMS value), and short-circuit current reaching 127.67 μA (peak-to-peak value) or 31.99 μA (RMS value) at 12.21 m/s flow velocity was achieved. This research presents a simple design to enhance the output performance of an FTENG by amplifying the fluttering amplitude. Based on the performance obtained in this study, the improved FTENG has the potential to apply in a smart city for driving electronic devices as a power source for IoT applications.