Kind of a sweet shirt, actually. (image via The Smoking Gun)
A Florida man (it's never an "Oregon man" or an "Illinois man," is it?) was arrested for welfare fraud while wearing a t-shirt (pictured above) that says "Jail Sucks!" He probably didn't realize how awesomely ironic his choice of clothing would turn out to be when he picked it out over his "Welfare Fraud Rocks!" shirt. Actually, that would have been equally ironic. This isn't the guy's first trip to the suckfest that is the slammer, either. He's been arrested many times before for burglary, drug possession, battery, and more. As one astute commenter put it: "jail sucks well how bout stop breaking the law dummy." Indeed.
Sources: The Smoking Gun