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In October 2010, Meester said she had been working with a band called Check in the Dark and had been writing for the last six months after being inspired by Country Strong.She revealed her influences, "I love Neil Young and Joni Mitchell, that style of music, and as far as songwriting I think that's where my heart is." Vera Wang selected her to be the face of the fragrance Lovestruck in 2011, stating that Meester's "beauty, talent and spirit will inspire all the young women that I hope will enjoy this passionate, new young fragrance." while Los Angeles Times wrote, "[Meester's] performance often has the feeling of a sports car in neutral.
But it's not an impersonation; it's a performance with its own comedy and sweetness." For the film, Meester recorded a cover of the song "Words I Couldn't Say" by Rascal Flatts as well as "A Little Bit Stronger" by Sara Evans featured on the film's soundtrack; a promotional single titled "Summer Girl"; and a duet with Garrett Hedlund titled "Give In To Me".
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." When she was 11 years old, Meester and her siblings moved with their mother to New York City.
She attended the Professional Children's School and began working as a model with Wilhelmina, booking a Ralph Lauren campaign shot by Bruce Weber, and working with then-photographer Sofia Coppola.
She has also modeled, having been the face of brands such as Jimmy Choo, Herbal Essences, and Vera Wang.
She has two brothers; an older brother, Douglas Logan Meester (born 1983), and a younger brother, Alexander "Lex" Meester (born 1994).
A recurring role in Entourage as Justine Chapin and Veronica Mars as Carrie Bishop followed in 20.