The traditional Chinese freehand brushwork spirit is the core aesthetic rooted in China’s local literary system. Different from the creative thinking of mechanically recreating objects in Western realistic art, freehand brushwork pays attention to conveying feelings with objects and expressing the spirit with form, and advocates that the creator’s subjective feelings and objective objects should blend with each other, which is also the core spiritual power to support the continuous inheritance and development of Chinese traditional art. Nowadays, Chinese and Western arts are deeply blended, and the localization and nationalization of oil painting have become the mainstream direction of domestic art creation. If we blindly apply the Western realistic and abstract solidified creation mode, it is difficult to create an artistic style with local cultural characteristics. In order to enrich the oriental aesthetic connotation of contemporary oil painting and improve the language system of localized oil painting art, this paper takes the core characteristics of the traditional freehand brushwork spirit as the breakthrough point and combines the unique material advantages of oil painting media to deeply analyze the aesthetic fit relationship between them. The paper further interprets the contemporary cultural value of the integration of freehand brushwork spirit into oil painting creation by exploring four practical paths, namely, image modeling, translation of pen and ink, construction of virtual and real artistic conception, and accumulation of creators’ accomplishment, so as to provide feasible theoretical reference and practical ideas for the innovative transformation and localization of traditional aesthetics in contemporary oil painting.