Descriptive word, sort of comparing ones self to an actual homeless person in relation to clothes, appearance, etc. It is not actually paying out homeless people, rather going for an appreciation of how terrible something really is. Meant to be used as humour.
"But when he suprised me after class, I looked totally homeless that day"
"And they left me at the party all alone, I was totally homeless"
"Why're you being so homeless for?"