up to date vs with-it

up to date and with-it both are adjectives.

Word	Noun	Adjective	Verb	Adverb
up to date	No	Yes	No	No
with-it	No	Yes	No	No

As adjectives, up to date and with-it are synonyms defined as:

up to date and with-it: in accord with the most fashionable ideas or style

Other synonyms of up to date include cutting-edge, up-to-date.

up to date (adjective)	with-it (adjective)
reflecting the latest information or changes	in accord with the most fashionable ideas or style
in accord with the most fashionable ideas or style	having the shrewd resourcefulness needed to survive in an urban environment