Flexible plants, fungi, and sessile animals are thought to reconfigure in the wind and water to reduce the drag forces that act upon them. In strong winds, for example, leaves roll up into cone shapes that reduce flutter and drag when compared to paper cut-outs with similar shapes and flexibility. During flash floods, herbaceous broad leaves aquaplane on the surface of the water which reduces drag. Simple mathematical models of a flexible beam immersed in a two-dimensional flow will also reconfigure in flow. What is less understood is how the mechanical properties of a two-dimensional leaf in a three-dimensional flow will passively allow roll up and aquaplaning. In this study, we film leaf roll-up and aquaplaning in tree and vine leaves in both strong winds and water flows.