Brooke, Peyton, Haley - One Tree Hill
Surprisingly, these three found themselves behind bars fairly often for various crimes like robbery, assault, and even fraud. It's even more surprising that Tutor Girl, Haley, has been behind bars the most. Oh, ladies. At least, their mugshots look good!
Ian - Shameless
In his final episode, Ian goes to jail for his role in blowing up a van as part of a protest against conversion therapy.
Spencer Reid - Criminal Minds
Dr. Spencer Reid spent most of Criminal Minds Season 12 in prison after being framed for a murder that occurred while he was traveling through Mexico to score drugs that would help slow down the onset of his mother's Alzheimers.
Maddie - Proven Innocent
Attorney Madeline is wrongfully convicted of murder and is represented by an attorney who was also wrongfully convicted as they explore the frequency with which wrongful convictions based on race or simply 'being at the wrong place at the wrong time' occur.
Ruzek and Atwater - Chicago PD
Though Ruzek and Atwater never technically served any time, they have gone undercover as inmates on a few occasions. I couldn't pass up on including them because honestly, they really make the orange jumpsuit look good.
Olivia Benson - Law & Order: SVU
No, Olivia wasn't a prisoner but rather, working undercover for a case involving a prison guard who was sexually assaulting and raping female inmates. While there, the inmate took a liking to her and she almost became a victim before her partner, Fin, who was working as an undercover guard, stopped him in time.
Wait! There's more TV Characters Who Look Good in Orange! Just click "Next" below: