Well-functionalized electronic materials, such as silicon, in a stretchable format are desirable for high-performance wearable electronics. However, obtaining Si materials that meet the required stretchability of over 100% for wearable applications remains a significant challenge. Herein, a rational design strategy is proposed to achieve freestanding serpentine Si strips (FS-Si strips) with ultrahigh stretchability, fulfilling wearable requirements. The self-supporting feature makes the strips get rid of excessive constraints from substrates and enables them to deform with the minimum strain energy. Micrometer-scale thicknesses enhance robustness, and large diameter-to-width ratios effectively reduce strain concentration. Consequently, the FS-Si strips with the optimum design could withstand 300% stretch, bending, and torsion without fracturing, even under rough manual operation. They also exhibit excellent stability and durability over 50,000 cycles of 100% stretching cycles. For wearable applications, the FS-Si strips can maintain conformal contact with the skin and have a maximum stretchability of 120%. Moreover, they are electrically insensitive to large deformations, which ensure signal stability during their daily use. Combined with mature processing techniques and the excellent semiconductor properties of Si, FS-Si strips are promising core stretchable electronic materials for wearable electronics.