Stretchable electronics may enable electronic components to be part of our organs-ideal for future wearable/implantable biodiagnostic systems. One of key challenges is failure of the soft/rigid material interface due to mismatching Young’ s moduli, which limits stretchability and durability of current systems. Here, we show that standing enokitake-like gold-nanowire-based films chemically bonded to an elastomer can be stretched up to 900% and are highly durable, with >93% conductivity recovery even after 2000 stretching/releasing cycles to 800% strain. Both experimental and modeling reveal that this superior elastic property originates from standing enokitake-like nanowire film structures. The closely packed nanoparticle layer sticks to the top of the nanowires, which easily cracks under strain, whereas the bottom part of the nanowires is compliant with substrate deformation. This leads to tiny V-shaped cracks with a maintained electron transport pathway rather than large U-shaped cracks that are frequently observed for conventional metal films. We further show that our standing nanowire films can serve as current collectors in supercapacitors and second skin-like smart masks for facial expression detection.