Cynthia Bailey

Bailey dated actor Leon Robinson and gave birth to their daughter, Noelle, on November 9, 1999. During pregnancy, she discovered a uterine fibroid. She chose uterine fibroid embolization to treat it and later partnered with USA Fibroids Centers to raise public awareness about treatment options.

She turned down marriage proposals from former NBA player Jayson Williams and music executive Russell Simmons. On July 24, 2010, she married club owner Peter Thomas at the Fernbank Museum of Natural History in Atlanta. The ceremony aired on The Real Housewives of Atlanta. Their relationship ended in divorce in March 2017. Following the split, Bailey purchased a home she named Lake Bailey.

She married sportscaster Mike Hill on October 10, 2020, in Acworth, Georgia. The couple divorced in 2022. In March 2025, Bailey began dating musician LePrince.

In April 2018, Bailey underwent surgery to remove a lipoma tumor from her left shoulder blade. The tumor was benign and the procedure was successful.

Bailey grew up in Tuscumbia, Alabama, where her father worked in an auto factory and her mother in a sewing factory. She won the title of homecoming queen at Deshler High School. A talent scout from Wilhelmina Models noticed her during a subsequent pageant competition. She worked part-time at a local mall to save money for relocation. At age 18, she moved to New York City and signed a five-year contract with Wilhelmina.

Modeling work arrived quickly. Bailey spent a year walking runway shows in Paris and Milan before returning to New York. She booked commercial campaigns for Maybelline, Target, and Oil of Olay. Her editorial credits included Vogue, Elle, Glamour, and Vanity Fair. Her June 1995 cover for Essence became one of the bestselling issues in the magazine's history, earning her a second cover in 1997. She also appeared in an Annie Leibovitz Vanity Fair shoot alongside Iman, Beverly Johnson, Naomi Campbell, and Tyra Banks.

Bailey expanded into screen acting during the 1990s. She secured the role of Roxanne in the 1990 film Without You I'm Nothing, winning the part over Naomi Campbell. Television guest roles followed on The Cosby Show and New York Undercover, alongside appearances in music videos for New Order and Heavy D.

Bailey joined the cast of The Real Housewives of Atlanta in 2010 for its third season. Bravo producers brought her in after her move to Atlanta with Peter Thomas. She stayed for eleven consecutive seasons. Her friendships, business launches, and family life anchored major storylines until her departure in 2021.

She transitioned to other television formats soon after leaving the franchise. In 2021, Bailey starred in the inaugural season of the Peacock spinoff The Real Housewives Ultimate Girls Trip. The following year, she competed as a houseguest on season three of CBS's Celebrity Big Brother, finishing in third place. She later returned to The Real Housewives of Atlanta as a guest and recurring cast member.

Bailey founded the Bailey Agency School of Fashion in Atlanta in 2011 to train aspiring talent. In 2013, she and Thomas published a relationship memoir titled Carry-On Baggage: Our Nonstop Flight. She subsequently launched accessory brands including CB VIOR and Cynthia Bailey Eyewear. In July 2019, she opened The Bailey Wine Cellar and an adjoining event venue named The Bailey Room in Atlanta's Grant Park.

Her acting career gained renewed focus in the 2020s. She secured recurring roles as Ndasia in BET's drama Games People Play and as Gloria in BMF. Her film appearances include the 2022 Lifetime movie Cruel Instruction, The Stepmother, and The Lost Holliday.

In October 2024, Bailey launched the podcast Humble Brag with Crystal and Cynthia. She co-hosts the weekly series with former The Real Housewives of Beverly Hills cast member Crystal Kung Minkoff, discussing entertainment news and reality television.