with-it vs up to date

with-it and up to date both are adjectives.

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

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

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

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

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