Jennings’ was known to press his fingers into his closed eyelids for inspired ideas created by the blotches of color which appeared. Calling himself the “sun, moon and star artist,” he often used these symbols of nature. He began using scrap lumber to make assorted whimsical pieces such as whirligigs, windmills, and Ferris Wheels.
Jennings' work has been considered to be a outlay of Appalachian art traditions which embrace abstraction. Jennings' work was influenced by dreams, visions, and occasional articles and books.