Myelination is fundamental to brain function, enabling rapid neural communication and supporting neuroplasticity throughout the lifespan. While hierarchical patterns of myelin maturation across the cortical surface are well-documented in humans, it remains unclear which features reflect evolutionarily conserved developmental processes versus human-characteristic adaptations. Moreover, the laminar development of myelin across the primate cortical surface, which shapes hierarchies and supports functions ranging from sensory integration to network communication, has been largely unexplored. Using neuroimaging to measure the T1-weighted/T2-weighted ratio in tissue contrast as a proxy for myelin content, we systematically compared depth-dependent trajectories of myelination across the cortical surface in humans and macaques. We identified a conserved "inside-out" pattern, with deeper layers exhibiting steeper increases in myelination and earlier plateaus than superficial layers. This depth-dependent organization followed a hierarchical gradient across the cortical surface, progressing from early maturation in sensorimotor regions to prolonged development in association areas. Humans exhibited a markedly extended timeline of myelination across both cortical regions and depths compared to macaques, allowing for prolonged postnatal plasticity across the entire cortical hierarchy - from sensory and motor processing to higher-order association networks. This extended potential for plasticity may facilitate the shaping of cortical circuits through postnatal experience in ways that support human-characteristic perceptual and cognitive capabilities.