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 ?
Well it would be a good starting point if we actually had progressive politicians. The Democrats lose because they have no substantive platform for actually helping people because doing that would go against their donors. To be clear, it’s the same for Republicans. There’s a reason why the government just ping pongs between the two parties. The only reliable base either party has is the one that’s more culturally aligned with them, whatever that means at the time.
If they literally ever credibly ran on basic issues like housing, food, healthcare and the elections were fair, they would win. But they don’t, because they can’t, so they will never have consistent support.