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Thornton Oakley (March 27, 1881 – April 4, 1953) was an American artist and illustrator.

Thornton Oakley was born on Sunday, March 27, 1881, in Pittsburgh. He was the son of John Milton Oakley and Imogen Brashear Oakley. He graduated from Shady Side Academy in 1897, and studied at the University of Pennsylvania, receiving B.S. and M.S. degrees in architecture in 1901 and 1902.

Oakley began his study of illustration with Howard Pyle in 1902, working with him for three years, both at Pyle's winter studio on North Franklin St. in Wilmington, Delaware, and at his summer studio in Chadds Ford, Pennsylvania, which was situated in the old mill that now houses the Brandywine River Museum. Almost half a century later, Oakley described his first day with Pyle in an address he delivered at the Free Library of Philadelphia, on the occasion of which he also presented his collection of Pyleana – drawings, prints, books and other items, including letters and sketchbooks – to the Free Library: