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Not to be confused with Caitlin Upton. Texas state tennis champion, and Jeff Upton, a high school athletics director. In 1999, Upton moved with her family to Melbourne, Florida, where she was a student at Holy Trinity Episcopal Academy. Upton attended a casting call in Miami for Elite Model Management in 2008 and was signed the same day.

In April 2011, an Internet video of her doing the dougie hip-hop dance at a Los Angeles Clippers game went viral and served to increase her popularity. Upton made an appearance in a June 2011 episode of Tosh. Celebrity Softball Game at Chase Field in Phoenix, Arizona, in July 2011. Upton's acting debut was in the film, Tower Heist, as Mr. It was released in November 2011. She also appeared in The Three Stooges as Sister Bernice.

Upton appeared on the cover of the 2012 Sports Illustrated Swimsuit Issue, released in February 2012. Upton has also recounted the negative aftereffects of the 2012 Sports Illustrated cover, as she was subjected to criticism and felt she had been objectified. She has appeared in advertising campaigns for David Yurman, Sam Edelman, Betsey Johnson, Guess? In 2012, she was ranked the fifth-sexiest model by Models. Hot 100 list, citing her photo shoots with Sports Illustrated. Upton was the cover model for the 2013 Sports Illustrated Swimsuit Issue for the second consecutive year. In September 2013, Upton was named Model of the Year at the 10th annual Style Awards at the Mercedes-Benz Fashion Week in New York.