She also starred in the films Sand Castles (2014), Pass the Light (2015), The Bride He Bought Online (2015), Mom and Dad (2017), and Night School (2018).

She originally planned to attend Southern Methodist University for her college education, but chose instead to relocate to Los Angeles in order to pursue her acting career.

From 2014 to 2016, Winters starred in the regular role of Emma Al-Fayeed in the drama series Tyrant,[5] created by Gideon Raff for the FX network.

Winters starred in a leading role in the 2014 independent drama film, Sand Castles, directed by Clenét Verdi-Rose, opposite actors Jordon Hodges and Clint Howard.

[10][11] In 2017, she appeared opposite Nicolas Cage and Selma Blair in the horror comedy film Mom and Dad, directed by Brian Taylor.

[15] Winters portrayed Chlöe Rice, the new head cheerleader and "it" girl of Liberty High in a recurring role of the second, third, and fourth seasons of Netflix's drama series 13 Reasons Why,[16] and appeared in the 2018 comedy film Night School, directed by Malcolm D.