Numerous studies have aimed to improve the mechanical flexibility of thin-film encapsulation, a key obstacle in commercializing wearable organic light-emitting diodes (OLEDs). This study develops a silbione-blended organic/inorganic hybrid epoxy polymer (hybrimer) with high toughness as an organic barrier to enhance the flexibility of organic-inorganic multi-barriers. The optimal silbione-blended hybrimer (SBH) films exhibit superior mechanical properties, including increased elongation and tensile strength, compared to the hybrimer. The 3.5-dyad SBH-based encapsulation achieves a water vapor transmission rate of 7.83 × 10−6 g/m2/day and 9.45 × 10−5 g/m2/day before and after bending at a strain of 2%, respectively. In addition, the SBH barrier effectively protects the inorganic barrier by forming a robust aluminate phase at the interface between the inorganic and organic barrier, even under harsh conditions of 85 °C/85% relative humidity, demonstrating its potential for wearable applications. As a result, SBH-based encapsulations offer mechanical and environmental stability, making them ideal for wearable OLEDs.