street smart vs with-it

street smart and with-it both are adjectives.

Word	Noun	Adjective	Verb	Adverb
street smart	No	Yes	No	No
with-it	No	Yes	No	No

As adjectives, street smart and with-it are synonyms defined as:

street smart and with-it: having the shrewd resourcefulness needed to survive in an urban environment

Other synonyms of street smart include streetwise.

street smart (adjective)	with-it (adjective)
having the shrewd resourcefulness needed to survive in an urban environment	in accord with the most fashionable ideas or style
	having the shrewd resourcefulness needed to survive in an urban environment