I understand it more than baseball managers wearing uniforms. A lot more.
Managers wearing uniforms makes sense to me, because it's just a tradition passed down from the period when it was as likely as not that the manager was also an active player. They don't much do that anymore, obviously, but the rules still support it, and as most managers are former players anyway and are more comfortable dressing in a uniform than a suit, the attire remained as it was through inertia.
On the subject of Torts, this doesn't bother me in the slightest. Many things about him do, primarily the hypocrisy and capriciousness, but this is less than nothing. No aspect of his attire impacts his ability to do his job, he can wear whatever he wants on the bench, within reason.