Judge Bailey was born in Charleston and raised in Belle.  She is a 1977 graduate of Hollins College and a 1980 graduate of West Virginia University College of Law and also completed classes at the University of Paris (Sorbonne) and l’institut d’etudes politique de Paris.

She practiced law in Charleston from 1980 to 1993, completing her practice as a partner with the firm of Hamb, Poffenbarger & Bailey.  Having worked during eleven legislative sessions for the West Virginia House of Delegates and one session for the West Virginia Senate, in 1993 she became the first full-time lawyer for the West Virginia Senate where she primarily served as Counsel to the Senate Judiciary Committee.

In 2002, she was appointed by the Governor to serve on the bench in the Thirteenth Judicial Circuit (Kanawha County).  She was thereafter elected in 2004, 2008 and 2016 and has served as Chief Judge in Kanawha County in 2008, 2013, 2017 and 2022. She was instrumental in establishing the Kanawha County Day Report Center and serves on its board.  Since its opening in 2009, she has presided over the Kanawha County Adult Drug Court, one of the first to be established in the state.  In 2016, the Drug Court celebrated the graduation of 100 participants since its inception.

She is the recipient of the 2002 Outstanding Public Servant Award by the West Virginia Trial Lawyers Association and has served on the Board of Directors of the West Virginia Legal Aid Society and on the Division of Juvenile Services Director’s Advisory Council.  She has also served on the committees for Dropout Prevention Summit Planning Group, Project INTER-CEPT (Interventions Needed To End Recidivism – Critical Entry Point Team) and on the Board of Recovery Point-Charleston, a treatment facility for women.

In 2017, she was appointed by the Chief Justice of the West Virginia Supreme Court of Appeals to serve as the West Virginia Chair of the Regional Judicial Opioid Initiative (RJOI), whose membership included representatives from Ohio, Tennessee, Illinois, Indiana, Kentucky, Michigan, North Carolina, and West Virginia. Additionally, she has served on the Board of Directors of the West Virginia Judicial and Lawyer Assistance Program (WVJLAP) since 2018.  In 2019 she became a Fellow of the West Virginia Bar Foundation.

Having served longer than any other female circuit judge in West Virginia, in 2022 Judge Bailey was honored to become the first female judge to serve as President of the West Virginia Judicial Association since it was established in the 1970s. She also previously served on the Legislative Committee and on the 2024 Judicial Realignment Committee, which made recommendations to the Legislature concerning legislation that was adopted in 2023 and effective in 2024.  Judge Bailey presently serves on the Executive and Education committees and as Chair of the Drug Court Judge Committee of the Judicial Association.

In addition to the State of West Virginia, she is admitted to practice in the United States District Court for the Southern District of West Virginia, United States Court of Appeals for the Fourth Circuit, and the United States Supreme Court.

She is a member of Christ Church United Methodist in Charleston, where she has served on the Board of Trustees and on the Staff Parish Relations Committee.

She is most proudly the mother of one daughter.