As one of the most renewable and sustainable resources on Earth, bamboo with its high flexibility has been used in the fabrication of a wide variety of composite structures due to its properties. A bamboo-based winding composite (BWC) is an innovative bamboo product which has revolutionized pipe structures and their applications throughout China as well as improving their impact on the environment. However, as a natural functionally graded composite, the flexibility mechanism of bamboo has not yet been fully understood. Here, the bending stiffness method based on the cantilever beam principle was used to investigate the gradient and directional bending flexibility of bamboo (Phyllostachys edulis) slivers under different loading Types during elastic stages. Results showed that the graded distribution and gradient variation of cell size of the fibers embedded in the parenchyma cells along the thickness of the bamboo culm was mainly responsible for the exhibited gradient bending flexibility of bamboo slivers, whereas the shape and size difference of the vascular bundles from inner to outer layers played a critical role in directional bending flexibility. A validated rule of mixture was used to fit the bending stiffness under different loading Types as a function of fiber volume fraction. This work provides insights to the bionic preparation and optimization of high-performance BWC pipes.