If you dress down in a context where formal attire is expected, it's a signal. What it signals depends on what happens. If you're shunned and avoided, then you're just a loser or a hobo. If you're clearly valued, listened to with interest etc, despite that mismatch, it is a countersignal. You could only afford to do this by having high status and importance in the community that outweighs such expectations. It doesn't matter if you simply don't care and never think about how you dress and this just comes naturally. The signal is still picked. The person to whom general expectations and rules don't quite apply the same way as to the average person is the one of higher status.
In other words, it's not enough to flaunt the rules, you also have to get away with it for it to count.
Reminds me of how Nassim Taleb (famous for Black Swan among other books) says that he wants his surgeon to look like a butcher. The thinking goes that if despite all that roughness and sticking out, he’s a surgeon, he must be a pretty damned good surgeon.