Miles is the youngest daughter of Jim and Cora Mae Miles of Bessemer. She learned to bake by helping her mother and an aunt, Queen Esther Miles, in the kitchen. She graduated from Wenonah High School in 1975 and took computer science classes at Alabama A&M University and Lawson State Community College. While in school she worked as a line cook at El Palacio in Homewood and then as a pastry cook at Vincent's in Riverchase.
Miles and her sister, Diane, were among the first kitchen staffers hired by Frank Stitt when he opened Highlands in 1982. Along with another cousin, Verba Ford, Miles worked her way into the pastry department. By the time Bottega Restaurant opened in 1988, Miles convinced Stitt to make her a full-time pastry chef, working with assistants Mark Christie and Cari Jolley out of Bottega's kitchen to prepare seasonal desserts for all four restaurants. Her pecan coconut cake is a popular mainstay on all four menus, and is featured in Stitts' cook books.
Miles has been nominated four times for the James Beard Foundation's award for "Best Pastry Chef". She was a semifinalist three times, and a finalist in 2016.
Miles has one daughter, LaToya, and two grandchildren. In 2013 she was diagnosed with diebetes.
- Carlton, Bob (April 8, 2016) "Highlands' Dolester Miles learned to bake from her mom, now she's competing with America's best for James Beard Award." The Birmingham News