I came across this today while searching for something else. It's a painting of a hand plane from the 14th century. That is the earliest depiction of a hand plane I have seen; I'm not sure how long hand planes have been in use but I'd guess much earlier than this. However it is always good to have evidence.
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Admittedly, my knowledge of tools in history is pretty limited, as is my knowledge of the ancient Roman philosophy that influences the subject matter in this painting. This image, a detail of the fresco
Allegories of Good and Bad Government painted by Ambrogio Lorenzetti in 1338-9, shows a woman holding a hand plane. If I find any earlier images I'll have to take note. For more details about this subject and lots of images of this and other frescoes, please see the marvelous book: Italian Frescoes, the age of Giotto, 1280-1400 by Joachim Poeschke ISBN-13: 978-0-7892-0863-7.