In many perennial wind-pollinated plants, the dynamics of seed production is commonly known to be highly fluctuating from year to year and synchronized among individuals within populations. The proximate causes of such seeding dynamics, called masting, are still poorly understood in oak species that are widespread in the northern hemisphere, and whose fruiting dynamics dramatically impacts forest regeneration and biodiversity. Combining long-term surveys of oak airborne pollen amount and acorn production over large-scale field networks in temperate areas, and a mechanistic modeling approach, we found that the pollen dynamics is the key driver of oak masting. Mechanisms at play involved both internal resource allocation to pollen production synchronized among trees and spring weather conditions affecting the amount of airborne pollen available for reproduction. The sensitivity of airborne pollen to weather conditions might make oak masting and its ecological consequences highly sensitive to climate change.