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Hipster or Homeless 

A game that is played historically in the inner Northern suburbs of Melbourne amongst gentrified youth. It was originally invented by a miss C Speldewinde during the years of her cultural enlightenment.
Let's play "Hipster or Homeless", I'll go first.... look at that guy over there in ripped jeans, 90's basketball jumper and scruffy beard. Hipster.... or.... homeless?!?
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homeless or hipster 

an expression native to the westcoast of BC used to describe the confusion that arises when you can't tell if someone has spent a lot of money and time, trying to achieve the..."I-just-woke-up-this-morning-and-rolled-out-of-bed-and-didn't-even-look-in-the-mirror look or literally doesn't have a home.
Walking down the street with your girlfriends....

"Hey, check out that dude up there."

"Hm I dunno, homeless or hipster?"

"Oh shit, totally homeless!"