Energy harvesting techniques can exploit even subtle passive motion like that of plant leaves in wind as a consequence of contact electrification of the leaf surface. The effect is strongly enhanced by artificial materials installed as ‘artificial leaves’ on the natural leaves creating a recurring mechanical contact and separation. However, this requires a controlled mechanical interaction between the biological and the artificial component during the complex wind motion. Here, we build and test four artificial leaf designs with varying flexibility and degrees of freedom across the blade operating on Nerium oleander plants. We evaluate the apparent contact area (up to 10 cm2 per leaf), the leaves’ motion, together with the generated voltage, current and charge in low wind speeds of up to 3.3 m s−1 and less. Single artificial leaves produced over 75 V and 1 µA current peaks. Softer artificial leaves increase the contact area accessible for energy conversion, but a balance between softer and stiffer elements in the artificial blade is optimal to increase the frequency of contact-separation motion (here up to 10 Hz) for energy conversion also below 3.3 m s−1. Moreover, we tested how multiple leaves operating collectively during continuous wind energy harvesting over several days achieve a root mean square power of ∼6 µW and are capable to transfer ∼80 µC every 30–40 min to power a wireless temperature and humidity sensor autonomously and recurrently. The results experimentally reveal design strategies for energy harvesters providing autonomous micro power sources in plant ecosystems for example for sensing in precision agriculture and remote environmental monitoring.