Off the top of my head, some things I think you really need to pay attention to if you're going to try and look homeless. These are things that might give you away:

- Shoes - They should be years old... not new
- Hands - Calused(sp?) and rough is better, if you have delicate hands, cover them with some crappy old work gloves
- Eyes/Face - Most homeless I've seen look "worn", or "tired". A long haired wig and some dirt might help
- Your smell - If you smell like Salon Selectives and Irish Spring, that will give you away faster than anything else.
- Shopping Cart - If it's not old, rusted out, and one wheel held together with shoestrings, then, you don't fit in! I also hear it is hip to have 2! Make sure you fill your cart with things that could be recycled, and things that look like "mementos".

I may make jokes, but that doesn't mean I don't respect them as human beings, in fact, you might actually learn something about survival by talking to someone who is homeless.