Meester was born in Fort Worth, Texas, the daughter of Constance (née Haas) and Douglas Meester.[2][3][4] At the time, her mother was serving a federal prison sentence for her involvement in a drug ring that smuggled marijuana from Jamaica to the United States. She 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.[2][3] At this time Leighton's grandmother cared for her.
Meester has maintained that her parents gave her a normal upbringing and, despite their criminal past, are good people with experience that has only made Meester more open-minded and non-judgmental, "It made me realize that you can't judge anyone—especially your parents—for what they've done in their past, because people change."[5] Meester has joked, "Look, I could've turned out a lot worse".[6] She has cited her mother as her style icon.[7]
Meester grew up in Marco Island, Florida, where she participated in productions at a local playhouse.[8] When she was 11 years old, Meester and her mother moved to New York.[8] Meester attended the Professional Children's School and also began working as a model with Wilhelmina, booking a Ralph Lauren campaign shot by Bruce Weber and working with then photographer (now film maker) Sofia Coppola[8][9] as well as many commercials including Tamagotchi toys and Clearasil. Meester made her television acting debut as a murder victim's friend on an episode of Law & Order.[8][9] At 14, Meester moved to Los Angeles, California, wanting more stable work, and attended Hollywood High School and Beverly Hills High School.[9][10] She then transferred to a small private school and graduated a year early.[11]
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