Smart in a worldly sense

• Savvy, in a way
• Like some urchins
• Like the Artful Dodger

Longman Dictionary of Contemporary English Word definitions in Longman Dictionary of Contemporary English
adjective EXAMPLES FROM OTHER ENTRIES ▪ a streetwise detective ▪ Copeland is a streetwise cop who knows how to take care of himself. ▪ He seemed very streetwise for a kid who had just left school. ▪ Kids these days are much more streetwise than we ever ...

Wikipedia Word definitions in Wikipedia
StreetWise is a street magazine sold by people without homes or those at-risk for homelessness in Chicago . Topics covered depend on what is happening in Chicago at the time. In 2003, it had the largest readership of any street publication in the United ...

Wiktionary Word definitions in Wiktionary
a. 1 Having the necessary knack, personality and instinct for survival in rough, urban environments. 2 Possessing a style that embodies the life and microculture located within urban settings, typically in the States.