Meester was born in Fort Worth, Texas, to Constance Lynn (née Haas) and Douglas Jay Meester. Her father is a real estate broker; her mother is a writer. She has two brothers; an older brother, Douglas Logan Meester (born 1983), and a younger brother, Alexander “Lex” Meester (born 1994). At the time of her birth, Meester’s parents were serving time in a federal prison for their involvement in a drug ring that smuggled marijuana from Jamaica to the United States. Constance was able to give birth to Leighton in a hospital and nurse her for three months in a halfway house, before returning to prison to complete her sentence. Her paternal grandparents cared for Meester during this period. She has maintained that her parents gave her a normal upbringing and, despite their criminal past, has stated, “It made me realize that you can’t judge anyone—especially your parents—for what they’ve done in their past, because people change. ” She grew up in Marco Island, Florida, where she participated in productions at a local playhouse. Her parents separated in 1992.