Dree Louise Hemingway Crisman was born in Sun Valley, Idaho, the daughter of actress Mariel Hemingway and Stephen Crisman, and the niece of the late model and actress Margaux Hemingway. Notably, she is the maternal great-granddaughter of renowned author Ernest Hemingway.
Growing up in Ketchum, Idaho, Dree attended Ernest Hemingway Elementary School before moving to California, where she resided in Westlake Village. She spent two and a half years at Oaks Christian High School before dropping out to pursue her modeling career. In 2003, she was presented as a debutante at the Bal des débutantes in Paris, France.
As a model, Dree has represented numerous major companies in print advertising and fashion shows. Her notable appearances include the fall/winter 09-10 catwalk show for Givenchy in Paris, the Calvin Klein resort show in New York, and the Topshop spring/summer 2010 show in London. She has also walked for prominent designers such as Shiatzy Chen, House of Holland, Karl Lagerfeld, Giles, Chanel, and Rue du Mail.
Dree has been the face of several high-profile campaigns, including Gianfranco Ferré, Salvatore Ferragamo, and Gucci. She has also appeared in editorials for Harper's Bazaar, i-D, V, W, Numéro, and multiple national editions of Vogue.
In addition to her modeling career, Dree has ventured into the world of film. She starred in the U.S. independent film Starlet (2012),directed by Sean Baker, and received the Robert Altman Award for the film at the 2012 Independent Spirit Awards. She has since appeared in supporting roles in films such as Listen Up Philip (2014) and While We're Young (2014). Furthermore, she appeared in the music video for "I Always Knew", a single from The Vaccines' album, "Come of Age".