With-it meaning

wĭth'ĭt', wĭth-
Interested in and sensitive to the latest styles and trends; up-to-date.
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Streetwise and knowing; savvy.
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Mentally competent.
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Sophisticated, aware, up-to-date, etc.
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Fashionable; stylish.
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Up-to-date on current fashion and trends.
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(slang) Aware of current trends and fashions.
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(slang) Attentive.

Jack is sick today and doesn't really seem with it.

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