It's not clothes that the homeless need, it's a kick up the rear and a healthy dose of education.
Pretty much every homeless person that I've met in the past are in that situation through their own life choices and through decisions which they made. They often just also accept it, and put up with it instead of trying to get themselves out of the situation. If the people tried, and stopped feeling sorry for themselves and actually sought and accepted the help that is out there then they would quickly be able to fix their self-given ills and actually become functional members of society. However, few will do this, and the cycle will continue.