Oakley was born in Kentucky and raised in Northeast Missouri. He attended University of Central Missouri in Warrensburg receiving a B.S. In Criminal Justice. While in law school he was an intern for Legal Aid of Western Missouri and participated in Appellate Advocacy Moot Court. In 2013, Oakley received his Juris Doctorate from the University of Missouri-Kansas City.

After graduating law school, he went on to live in China for over a year. While in China Oakley taught English, studied Chinese and traveled across the country. He also met his future wife Katya who had come from Russia to study Chinese.

In his spare time he enjoys traveling, reading and spending time with Katya.