Very seldomly do people actually plan to go to prison. Sometimes they do if they are planning to break someone out which requires them to infiltrate the inside, but I can't help but feel like that's very rare. That's why my mom always gave me the best advice: "always leave the house dressed for jail." People are going to remember you for your mugshot, so at least if you're wearing a suit people will assume your crime was nothing more serious than tax fraud or embezzlement.
In a way, this man did dress for jail. He went the ironic route, and who doesn't like a little bit of irony? I'm sure his shirt was a great conversation starter with some of the other prisoners. Making friends is important, even if your only choices are murderers and thieves.