I think progressives never thought about this because we banked on immigration and demographic change allowing us to win culturally and electorally but the issue is immigrants tend to be overwhelmingly male, that is how Trump won actually he won over a lot of Hispanic,Black,Asian and indigenous men who feel humiliated by a new culture, economy and world.
So what can we do rhetorically and policy wise to win more young men over ?
Education. You will never be able to explain taxes in a way that can counter propaganda if the person is an idiot. You just won’t. And until then it’s an uphill battle.