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Something said to someone meaning that they should not be ashamed of anything or that they shouldn't be sad. It means that they should not stare at the ground in despair but rather pick their head up and stand tall.
Jim: John, why are you so sad?
John: I fucked Sally Parker and she's pregnant.
Jim: Sally Parker?! She's hot as fuck. Head up.

Jim: We just lost the state championship. I am so sad.
John: You guys are a great team and came a long way. Head up.
by John Fuckerino December 09, 2013
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3
When someone is "head up" they are angry or frustrated. It is mostly a Southern saying. You can hear it being said in The Rescuers film and other movies with Southern people.
When Gramps gets head up, his nose gets plumb outta joint
by DallasDeckard February 22, 2011
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