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 ?
I always make the same argument as to why left-wing politics has been so generally unappealing to working-class, average people - in spite of the irony. I vote left, I have a uni degree, and they still piss me off. Don’t talk about Marxist analyses, and don’t make everything about gender identity or Palestine (I care deeply about Palestine, but it’s not the main issue that I’d want my local political party to focus on) make it about the issues facing regular people on an every day basis. Say “bro, me like taxes” instead of producing a 20-page paper on the evils of capitalism.