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Synonyms for With-it (same or very similar meaning)

WordNet sense 1 (in accord with the most fashionable ideas or style):
up-to-date, cutting-edge

WordNet sense 2 (being or in accordance with current social fashions):
fashionable, stylish

WordNet sense 3 (having the shrewd resourcefulness needed to survive in an urban environment):

WordNet sense 4 (showing mental alertness and calculation and resourcefulness):

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