We have to admit, the prison break genre has to be one of our greatest guilty pleasures. It's just behind rad 80s hair metal and cheesy romantic comedies from the 90s. (We're very complicated.) There's just something captivating about the roguish feat of reclaiming freedom. We've watched just about every prison-themed movie that we can get our hands on, and we've read The Count of Monte Cristo more times than we can count. (We're also huge fans of Alexandre Dumas and his Musketeer-themed tales.) Just think of all those amazing scenes! There's that brilliant moment in The Shawshank Redemption when Andy bursts out of the mud. O Brother, Where Art Thou has a ton of charm, from beginning to end as the trio gallivants their way across the countryside. And The Great Escape? Well, we don't need to tell you how much of a masterpiece that film is. When Orange Is the New Black came out, we binged each season without holding back!

With all of these great stories to tell, it's no wonder that prisoner costumes are a popular choice for Halloween and costume parties. Maybe you want to showcase your wilder side by skirting some of the party rules, or you want to recreate some iconic scenes from your favorite movies. There are a ton of great reasons to wear one! And since we're one of the top authorities on the web when it comes to costumes, we just had to make sure we carried all of the best prisoner costumes. We have tons of different styles, from old-timey looks that will have you working on the chain-gang, to modern, bright orange style outfits. We have something that will fit your sense of law-bending fashion, and we're here to help guide you in your choice!

Wearing a prisoner costume is all about embracing your rebellious side! That means throwing the normal rules out the window to follow your own rules at the party. It also means making sure you have a daring style that flies in the face of standard fashion regulations. If you want to indulge in that rebellious side, then you have a few options to get into character. Twenties gangster outfits, pirate outfits, and even Harley Quinn costumes are some examples. Those are pretty great choices to flaunt your inner defiance, but we really don't think you can find a more rebellious look that one of our women's prisoner costumes. Lucky for you, we carry a variety of styles, whether you want something a little more classic with black and white stripes or you're looking for something with a bit of a sexy spin on it. Check out some of our favorite options below!

Are you the kind of guy who never makes it onto Santa's nice list? Well, some boys were just born to be bad! During childhood, they were the class clown. During the teen years, they were the high school outlaw. And when they're all grown up? Well, that's when they're wearing the coolest costumes! If you're one of those bad boys all grown up, then you could try to get on Santa's good side this year by dressing up as an angel and committing yourself to doing good deeds. Or you could go the more entertaining route and go full rascal by turning yourself into a rebellious inmate fresh from a jailbreak. (Make sure to queue up some Thin Lizzy when you do it!) If that's how you want to roll, then you're going to have to make an important choice: which one of our men's prisoner costumes are you going to wear? We carry some classic striped outfits, some bright orange jumpsuits, and even some playful cat burglar costumes to help suit your tastes. We've put together some of our favorites below.