Oakley received his B.S. degree from Northwestern University and his M.S. and Ph.D. degrees from the University of Michigan. He has received numerous awards for his teaching and for his innovative use of technology in education, including the Luckman Distinguished Undergraduate Teaching Award from UIUC in 1993, the Outstanding Teacher Award from the American Society for Engineering Education (ASEE) in 1993, the Educom Medal in 1996, the Educational Activities Board Major Educational Innovation Award from the Institute of Electrical and Electronics Engineers (IEEE) in 1996, the Meritorious Service Award from the IEEE Education Society in 1998, the Third Millennium Medal from the IEEE in 2000, the Engineering Alumni Society Merit Award from the University of Michigan in 2003, and the Sloan-C Award for the "Most Outstanding Achievement in Online Teaching and Learning by an Individual" in 2003. He is a Life Fellow of the IEEE, a Fellow of the Online Learning Consortium, a Fellow of the ASEE, and a former Vice President of the ASEE.