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Hobo chillin is when you dress like a homeless person and have even been mistaken for a hobo because of your clothes. You might be wearing a raggedy shirt with holes or discolored ripped up pants. But really you have some Yeezy Season on worth like $20,000 and some Gucci flip flops. Things that you do to add to this hoboness are: messy hair, no makeup and not wearing your jewelry. The term Hobo chillin was first mentioned publicly was white Iverson himself, POST MALONE.
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