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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.
Post Malone on 106 K. MEL Interview:

"People on the street think am a hobo and they avoid me, hey guys i'm not a hobo...
i'm just hobo chillin"

"So I was wearing my Kanye West Season 2 shirt and they were supreme sweat pants and I was just barefoot...

...I'm not a hobo, I just don't have my jewelry on"
via giphy
by GoalDigger January 19, 2016
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