With-it Definition

wĭthĭt, wĭth-
adjective
Interested in and sensitive to the latest styles and trends; up-to-date.
American Heritage
Sophisticated, aware, up-to-date, etc.
Webster's New World
Fashionable; stylish.
Webster's New World
Streetwise and knowing; savvy.
American Heritage
Mentally competent.
American Heritage
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(slang) Aware of current trends and fashions.

Wiktionary
(slang) Attentive.
Jack is sick today and doesn't really seem with it.
Wiktionary

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