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