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Caleb Nichols from Westworld

In season 3 of Westworld, Caleb Nichols (played by Aaron Paul) joins up with Dolores after he helps her when she is injured.  Dolores shows Caleb the extent to which his life is controlled and his fate determined by others in order to recruit him to her cause.  As a veteran, Caleb suffers with some amount of PTSD and survivor’s guilt.  When season 3 begins, Caleb works construction with a robot companion, while also completing criminal acts after hours for additional cash.  Whether dressed for work, criminal activity, or infiltrating a 1%ers party, Caleb typically wears clothing that is dark grey or black.  Prior to his recruitment by Dolores, Caleb wears coveralls with orange pocket flaps to his construction job.

Rust Cohle

In the HBO series True Detective, Detective Rustin Spencer “Rusty” Cohle (Matthew McConaughey) is brought in as partner of Detective Martin Hart (Woody Harrelson) to solve a ritualistic murder in rural Louisiana. Dress up as either the buttoned-up 1995 Cohle or the broken-down 2012 version who’s now a suspect.

Hannah Horvath

In the HBO series Girls, Hannah Horvath (Lena Dunham) stars as a hip twenty-something from Brooklyn. She aspires to become a famous writer, but manages to bungle up pretty much everything, including her outfits, along the way.

Larry David

Larry David is star of Curb Your Enthusiasm and co-creator of Seinfeld. He likes to dress for comfort as he makes you cringe in discomfort by throwing all social norms out the window.

Omar Little

In the Wire, Omar Little is the modern-day Robin Hood robbin’ the hood. He’s a legendary stickup man with a heart of gold. You got the briefcase. He got the shotgun, the vest, and the jacket yo.

Carrie Bradshaw

Carrie Bradshaw is many things: a writer, a lover, and a best friend. Most of all, she is a fashionista and a shopping addict. See here, her most iconic outfit worn in the opening credits of “Sex and the City”. It includes a pale pink top, vintage tutu, and a wild mane.