Bailey grew up in a small town in the Bay Area called Half Moon Bay, CA. She began playing volleyball with her school team when she was 9 years old and joined a club team when she was 11. Bailey has grown up playing at multiple different clubs around the Bay Area, finishing her last two years at City Beach Volleyball Club as a setter. She then went on to play Division 1 indoor volleyball at College of the Holy Cross in Massachusetts. After a year on the East Coast, Bailey decided it was time to get back to California and transferred to Loyola Marymount University where she played both indoor and beach volleyball. In her sophomore season at LMU, the team made it to the second round of the NCAA Tournament in 2018.