WordWeb Online

1. In accord with the most fashionable ideas or style
   "a with-it boutique"; "add a sleek look to this with-it kitchen";
   - up-to-date, up to date, cutting-edge, nouveau
    
2. Having the shrewd resourcefulness needed to survive in an urban environment
   "The with-it child escaped from the gang";
   - streetwise, street smart

See also: fashionable, hip [informal], smart, stylish