Albert Barnes Commentary 2 Kings 19:21

"This is the word that Jehovah hath spoken concerning him: The virgin daughter of Zion hath despised thee and laughed thee to scorn; the daughter of Jerusalem hath shaken her head at thee." — 2 Kings 19:21 (ASV)

Concerning him—that is, concerning Sennacherib. The verses in 2 Kings 19:21–28 are addressed to the great Assyrian monarch himself and are God’s reply to his proud boasts.

The virgin, the daughter of Zion—The holy eastern city, Zion, is here distinguished from Jerusalem, the western one. Zion is given the remarkable title “virgin,” which is not applied to her sister city, probably because the true Zion, the city of David, had remained unconquered from David’s time, having never been entered by an enemy.

Jerusalem, on the other hand, had been captured by both Shishak (1 Kings 14:26) and Jehoash (2 Kings 14:13). The personification of cities as females is a common biblical figure of speech.

Has shaken her head at you—This was a Hebrew gesture of scorn .