Alkenylbenzene skeletons represent one of the most widely occurring structural motifs in pharmaceutical drugs, natural products, and advanced materials. The construction of alkenylbenzenes is promising through the use of a straightforward oxidative alkenylation protocol, particularly from unactivated alkenes. This is significant because unactivated alkenes are inexpensive raw materials that can be obtained in bulk quantities from petrochemical feedstocks and renewable resources. However, controlling the reactivity and regioselectivity of olefination with unbiased olefins remains a significant challenge, necessitating continuous efforts and potentially having a substantial impact on both organic synthesis and the industry. This review aims to provide an overview of the latest advances in regiocontrol strategies for oxidative alkenylation reactions with unactivated alkenes, which can be categorized into three types: 1) ligand‐promoted/accelerated reactions; 2) prefunctionalized olefins‐facilitated reactions; 3) directing group‐induced reactions.