Mark Reay is a former model, actor, and fashion photographer who was homeless in NYC for six years. Homme Less is a documentary on Reay; here's a trailer:
So began a period of my life sleeping rough. It was pretty tiring, and I didn't have much luck with the photos, but I stuck it out. I've never let the lack of money stop me having a good time, and I still had (dwindling) savings from my modelling. It was a happy time. At night I would always treat myself to a rotisserie chicken, but I always wanted a chilled rosé with it. So, in the afternoon, I would sneak into a minimarket, get the cheapest one from the shelf and hide it under the frozen peas. Then, at night, I would put on a fresh shirt and go to one of the fancy bars with my wine in my bag. Again, maybe because I had a certain look, no one ever checked my bag. I'd just go in, nick a glass off the counter and drink my wine surrounded my millionaires.
You can get away with anything if you're confident. Oh, and male, white, and good looking.