Bailey was born as Daisey Flowers officially on 30 March 1896 – her family claimed she was one year older – in Watertown, Tennessee. She was married first to Will Reedy, and had two sons, Robert and S. T., and two daughters, Fannie and Frankie. She worked on a plantation as a housekeeper and woodcutter. After Reedy’s death, she later married John Bailey.
Bailey relocated to Pontiac, Michigan, in 1943, where she worked as a housekeeper and babysitter. She lived independently until 1989, when she moved in with her granddaughter, Helen Arnold. She outlived all four of her children. Her hobbies included vegetable and flower gardening, listening to blues, as well as dancing and cooking.
As a supercentenarian, Bailey was reported to show signs of dementia, took blood pressure medication, and had surgery for cataracts, but was otherwise in good health. She claimed that the secret to her longevity was eating numerous vegetables daily, and the occasional drink of bourbon. She never ate beef but ate pork regularly.
Bailey stopped eating a few days before her death on 7 March 2010 at the age of 113 years, 342 days. Her cause of death was organ failure. She was survived by several grandchildren, as well as 70 great-grandchildren, 30 great-great-grandchildren, and 69 great-great-great-grandchildren.