Van Winkle was born in Victorville, California, the middle of three children of Sally (née Fitzgerald) and Charles Van Winkle. When he was two years old, his family moved to Oscoda, Michigan. When he was eight, his family moved again to Peachtree City, Georgia, where he graduated from McIntosh High School and attended the University of West Georgia but did not graduate, leaving at age 20 to pursue his acting endeavors in Hollywood.
Van Winkle made his television debut in a December 2004 episode of the Fox sitcom Quintuplets, and has since appeared in shows such as That's So Raven, Malcolm in the Middle, The O.C., and 7th Heaven. His film credits include one of the leads in Fox's Meet the Spartans, David R. Ellis's film Asylum, Universal's Accepted and Michael Bay's Transformers. While he has modeled for Abercrombie & Fitch shot by Bruce Weber, Van Winkle appeared in New Line/Paramount's 2009 reboot of Friday the 13th (another Bay production) as Trent Sutton-DeMarco, the character he previously portrayed in Transformers. He also appeared in Julianne Hough's 2008 music video for "That Song in My Head".
In 2011, Van Winkle starred in the suspense thriller film 247°F co-starring Scout Taylor-Compton. In 2012, he starred in the independent comedy Last Call. He also appeared in the thriller Bloodwork, co-starring Tricia Helfer.

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