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The word 'Skollie' is of South African (Afrikaans) origin and has many meanings:

A naughty, dirty or ill-mannered child.
A gangster or somebody who deliberately breaks laws.
Somebody who is devoid of class and manners.
A homeless person.

It can also be used to describe somebody's behaviour.
'Michelle, can you please control your children, they're acting like little skollies.'

'Yoh man, what Kanye West did to Taylor Swift at the VMA's was so skollie.'
by Saffa101 September 15, 2009
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2
noun

A rebel, revolutionary. A person who rejects the status quo and seeks a higher purpose.
It took balls for Kanye West to drop out of college and pursue his rap dreams. That's a skollie move.
by JuliusE August 24, 2011
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