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1.
A slang term used by fundamentalist Americans to describe a demographic of impressionable youth culture who demonstrate their attraction to popular rebellion by wearing their headgear in a manner that does not protect them from the sun.

Traditionally single males between the ages of 13 and 30 with no disposable income, but they dispose of it anyway. Instead of buying groceries they'll buy fast food, and instead of paying rent they live with others. Their excessive time and limited money goes into clothes, video games, movies, alcohol, pot, and minimum payments on a loan for a car that doesn't run.
"I went to go see the new Jason Statham movie, and a bunch of crooked hats were behind me yelling 'Ohh snap!' like every 5 minutes."

"I went to see the new The Fast and the Furious movie, but I couldn't see the screen over all the gold stickers on the crooked hat's crooked hats."

"I went to go see the new Gerard Butler movie, but I couldn't hear anything over the sound of all the crooked hats fapping to the sight of him."

"I went to pick up the new Call of Duty/Halo/Battlefield/ any FPS but I had to stand in a line of crooked hats and listen to them talk about how much they smoke weed, fuck bitches, and rape lives in video games. The seconds were like hours."
by Blank-Disk April 06, 2013
 
2.
to represent the hood you are from, no matter where you are from
I'm wearing Phat Farm Jeans, black Timberland Boots, and a crooked hat to the club. I'm reppin Harlem. Harlem son, what!!!
by tmoney2006 July 06, 2006