I understand the marketing. A law firm hands a homeless guy a t-shirt. Probably write it off as a donation. Probably feel good because they're providing clothing to someone, along with free advertising. Telling those of us who are oppressed or downtrodden that a lawyer in a white Maserati has our back. But this is a planted representative of the law firm, given a t-shirt specifically for advertising. OK, not exactly, but I bet some law firms have sued for whatever might distract a driver.
I'd probably have to prove intent. If the t-shirts were just given out at homeless shelters, I can't prove as much. However, if a shirt is handed to someone who is actively in traffic and panhandling, I think it's clear that the intent is for that person to wear the advertising. I guess I'd have to ask.
I'd also have to prove the t-shirt is distracting enough to be a problem. The person I saw today was in the middle of traffic on Beach and Kernan. Even an annoying sign jockey usually hangs out only on the sidewalk, and they don't interact with motorists. I'd say a panhandler is more distracting, but is the shirt playing a role in that? To me, it was, since I was trying to read it. But I can't speak for all motorists.
I know we have a program to get rid of those signs people put up along boulevards. That's basically what this is, but it really goes deeper. This is free advertising meant to make the consumer feel the company cares about another human, but is the person wearing the shirt getting paid for the advertisement? Even if it was a cash and shirt transaction, does it make the wearer an independent contractor that represents the company? Perhaps.