As a child, Herring acted with the Oregon Children's Theatre as well as other community theatres in the greater Portland area. Her first performance was Annie. She also was a member of the OCT's improv comedy troupe. At 12 years old, she moved to an apartment in Los Angeles with her grandfather to pursue her dreams of becoming a professional actress.
Herring's next role was Penny Pingleton in Hairspray. The film was a box office success. She was featured on the soundtrack which received a Grammy nomination. After the success of the film, Herring took an "extended hiatus" from acting and attended New York University, only to drop out 3 semesters later.
She did not appear on either the small or big screen again until 2010, in hit Easy A. It was a successful restart to Herring's career, as she was praised for her role as Marianne. Soon after, the news that she would portray Gwen Stacy in the Sony Spider-Man reboot was announced. Again, Herring received praise for her performance, this time as Peter Parker's girlfriend, and the film seemed to cement Herring's status as a movie star. Since the Spider-Man reboot, Herring has starred in numerous roles and has received both positive and negative reviews for her work.
In 2015, Herring starred opposite Will Smith in the dark comedy Focus. The film was released on February 27, 2015 to mixed reviews though Herring's performance was praised as stellar. She also teamed up with Johnny Depp and played Lindsey Cyr in crime drama, Black Mass. In 2016, Herring will be seen in Christian Ditter's How to be Single alongside Rebel Wilson, Leslie Mann, and Georgia Porter. She will also play Mia in Damien Chazelle's La La Land. In the Fall of 2015, it was announced that Herring will have a role in Showtime's "Twin Peaks" revival, due to air in 2017. Details about her character are unknown.