Self-healing waterborne polyurethane elastomers, as functional materials, have been widely applied in flexible wearable devices. However, inevitable crack damage during use significantly limits their service life. Achieving an optimal balance between mechanical strength and self-healing ability remains a major challenge in the development of high-performance self-healing polyurethane materials. In this study, a rigid-soft phase-separated structure with multilayered rigid and flexible supramolecular segments was designed using isophorone isocyanate (IPDI), dimethylglyoxime (DMG), and 6-methyl-1,3,5-triazine-2,4-diamine (AGM) as hard segments, and polytetramethylene ether glycol (PTMEG) as soft segments. AGM establishes a multi-hydrogen bonding network with urethane groups, and DMG introduces dynamically reversible oxime–carbamate bonds, enabling the PU elastomers to achieve a self-healing efficiency of up to 95.5%. Benefiting from the gradient rigidity of the polyurethane, the strong hydrogen bond formed by the urea–carbamate bond and the triazine ring, the elastomer exhibited excellent mechanical properties, with a tensile strength of 33.04 MPa, an elongation at break of 954.79%, and a toughness of 90.66 MJ m⁻³. Moreover, when the composite conductor was used as an electronic skin, it possessed good self-healing properties with electrical response properties.