I plan to dress like I am homeless when going out.
Do you think your friends would think this was a cool thing to do?
I do not have any friends.
It is not a good idea to dress up as a homeless person and pretend to be one; that is like mocking them. If you are interested in homeless people, it would be better to volunteer at shelters and get to know them.
I will know if I try.
Pretending to be homeless is a pretty mean thing to do. It is like you are making fun of anyone who is homeless and making a mockery of them.