Wiley was raised in Washington, D.C.[1] Her parents, Christine and Dennis W. Wiley, were co-pastors of the Covenant Baptist United Church of Christ (CBUCC) until 2017; they have been described as "pillars of the LGBT religious community", as the CBUCC was the only Baptist church in D.C. performing same-sex civil unions in 2007, prior to the eventual legalization of same-sex marriage.

[10] When the Netflix television series Orange Is the New Black —based on Piper Kerman's memoir of the same name— came into development, Wiley was told about the auditions by a friend from Juilliard, Marco Ramirez, who was a writer for the show.

[12] Her character's childhood and adolescence as a traveled, educated and strictly-disciplined "military brat" are explored, in addition to the chain of events leading up to her incarceration.

[14] In 2015, Wiley featured in the 21st episode of the 16th season of Law & Order: Special Victims Unit, "Perverted Justice", portraying a young adult wishing to recant her rape accusation of her father when she was 6 years old, and set him free.

In December 2015, it was announced Wiley had been cast to voice the titular character in the video game The Walking Dead: Michonne.

[18] Wiley was featured in Maniac Magazine, appearing on the cover and in an editorial of the 2014 September/October issue displaying "a series of bold, chic, high fashion looks.

According to the Human Rights Campaign's website, Wiley was always accepted and embraced by her parents, regardless of her sexuality, and to this she attributes her success.

[26] On October 4, 2016, Wiley announced her engagement to Orange Is the New Black writer Lauren Morelli and they married on March 25, 2017.