1. Having the necessary knack, personality and instinct for survival in rough, urban environments.
    Like all serial killers, he had the ability to sense vulnerability among potential victims; he didn't take the streetwise girls, he was after the younger women. -Ann Rule speaking about Gary Ridgway.
  2. Possessing a style that embodies the life and microculture located within urban settings, typically in the States.
    You could tell from the way he spat old Tupac lyrics, loitering in the corner with his homies, flipping that Yankees cap on his head like he couldn't give a damn that he was streetwise enough to melt Will Smith.

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Offline English dictionary