What is Flags?
1.
Word used for stamps in Prison. (i.e. a flag is often pictured on a stamp)
I'll give you 5 flags for the old issue of Buttman.
See
2.
Gang colors. Some people say that if more than 50% of your clothing is red or blue, you're "throwin flags"
Most often people won't think you're in a gang unless you're wearing lots of red or blue along with a red or blue durag and hat.
"Niggas wearin flags cause da colors match their clothes/They get caught in the wrong hood and filled up wit holes muthafucka" - 50 Cent