Sally Brown

Sally Brown has a lot of things on her mind, like moving into her big brother’s room. Fashion isn’t at the top of her list of concerns, so she keeps it simple with polka dots only. Luckily for you this look can also be passed off as rockabilly. People will never suspect that you’re coping the style of a child, a cartoon one at that.

Rae Doole from Black Snake Moan

In Black Snake Moan, Christina Ricci plays Rae Doole, a nymphomaniac held captive by a religious farmer who’s set on curing her of her sinful ways. As you might expect, she spends most of her time scantily clad in little more than chains, but she eventually trades them in for an old fashioned dress.

Travis Touchdown

In the video game No More Heroes, Travis Touchdown is a 20-something-year-old otaku, who spends his days collecting wrestling masks and watching anime. When he runs out of money to buy video games, he takes a job as a hitman.

Piper Chapman

Piper Chapman (Taylor Schilling) is a fish out of water at Litchfield prison. A white collar worker, she gets imprisoned when she’s caught transporting drug money for her dealer girlfriend. The uniform looks comfy, but I wouldn’t call orange the new black.

Pennsatucky

In Orange is the New Black, Tiffany “Pennsatucky” Doggett (Taryn Manning) is a bible-thumper convicted of murder and locked up in Litchfield Prison. She has rotten teeth from years of meth abuse, but she did clean up nicely for the Christmas pageant.

Red

In Orange is the New Black, Galina “Red” Reznikov (Kate Mulgrew) runs the prison kitchen, not to mention a lot of the behind-the-scenes business. As a mother figure, she’ll take you under her wing, but if you cross her, you’ll be sent to bed without dinner.

Happy Gilmore

Happy Gilmore is an unsuccessful ice hockey player who discovers he has a powerful slapshot-style golf swing. With the help of Chubbs he learns to improve his putting and control his angry outbursts in an effort to win the Pro Golf Tour against Shooter McGavin.

Robbie Hart

Robbie Hart wanted to be a rock star but life decided otherwise. Instead of ripped jeans and a leather jacket, he wound up donning a suit and tie as a professional wedding singer. Failed career or not, he was still able to get the girl and impress Billy Idol.

Holly Golightly

Audrey Hepburn plays one of her most iconic roles as Holly Golightly in Breakfast at Tiffany’s. Holly transforms herself from a country girl into a Manhattan socialite, who’s goal is to marry rich. You can complete her look by having breakfast in front of a Tiffany & Co. storefront.

The Girl in The Seven Year Itch

Marilyn Monroe plays The Girl in The Seven Year Itch, in which she’s the object of her neighbor’s fantasies. It’s in this movie that one of the most iconic images in film takes place – she stands over a subway grate which causes her dress to billow in the breeze.