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fly means to stay in style. so..

stay fly means to stay in style
"i gotta stay fly-y-y-y-y-y
till i die-e-e-e-e-e" - Stay Fly Three 6 Mafia
by dpz February 12, 2007
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1. To be awesomely cool.
2. Good looking.
3. Laid back.
4. epic.

"Hey, that Jordan guy, he Stays Fly 24/7."
by Norgo April 6, 2009
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