Most with-it is a phrase used to describe someone who is highly fashionable or up-to-date with the latest trends. Antonyms for this phrase could include words like outdated, uncool, unfashionable, antiquated, and behind-the-times. Someone who is described as outdated may have a style that was once popular, but is no longer in vogue. Uncool might suggest that they lack the ability to keep up with the latest trends or simply aren't interested in trying. If someone is described as being unfashionable, they may be wearing clothes that are not in sync with the current fashion climate. Finally, someone who is behind-the-times is one who is not current or keeping up with the latest developments in any industry.