Antonyms of adj with-it

2 senses of with-it

Sense 1
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"; "cutting-edge technology"; "a with-it boutique")

INDIRECT (VIA fashionable) -> unfashionable, unstylish -- (not in accord with or not following current fashion; "unfashionable clothes"; "melodrama of a now unfashionable kind")

Sense 2
streetwise, street smart, with-it -- (having the shrewd resourcefulness needed to survive in an urban environment)

INDIRECT (VIA smart) -> stupid -- (lacking or marked by lack of intellectual acuity)

Similarity of adj with-it

2 senses of with-it

Sense 1
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"; "cutting-edge technology"; "a with-it boutique")
       => fashionable (vs. unfashionable), stylish -- (being or in accordance with current social fashions; "fashionable clothing"; "the fashionable side of town"; "a fashionable cafe")

Sense 2
streetwise, street smart, with-it -- (having the shrewd resourcefulness needed to survive in an urban environment)
       => smart (vs. stupid) -- (showing mental alertness and calculation and resourcefulness)