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Adjective with-it has 2 senses
latest, last, newest, up-to-date, cutting-edge, with-it - in accord with the most fashionable ideas or style; "wears only the latest style"; "the last thing in swimwear"; "knows the newest dances"; "cutting-edge technology"; "a with-it boutique"Antonyms:  unfashionable, unstylish (indirect, via fashionable)
 
streetwise, street smart, with-it - having the shrewd resourcefulness needed to survive in an urban environmentAntonym:  stupid (indirect, via smart)
 
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