with it
cool; be on top of things; in the know; in with current styles or trends.
"Tyrell has one hella nice new Escalade!"
-"Yeah, that boy's always with it."
~or~
"I'm so freaked out about this date."
-"Dude, will you just get with it?"
-"Yeah, that boy's always with it."
~or~
"I'm so freaked out about this date."
-"Dude, will you just get with it?"