By the way, "my criticism towards men who shave their chests had nothing to do with obsession over appearance, but instead any man's understanding towards a woman" isn't very clarifying.
Are you telling me that men who shave their chests don't understand women? Because I've been told by many heterosexual women who date men that are straight who date women that they prefer their partners with shaved chests. Are we missing a point?
And I actually don't think that the stereotype that men cry are the perfect men is true. I actually believe the opposite. I believe the stereotype is that men who don't cry are strong providers.
The "tough" stereotype as attractive comes from the older tradition that men were responsible for providing a solid household while a woman's sphere of influence was within the home. To be "tough" meant mentally and economically stable. This point of view came to a large height in a revival of European chivalric ideals through the filter of an American aesthetic. This was a reaction to the "dandy" styles and fashions of the late nineteenth century which many religious leaders condemned as self-loving and masturbatory. Therefore a more rural, physical-based stereotype of masculinity was valued over a psychologically quick, if showy one as popularized by Mark Twain and Oscar Wilde.
Overtime this view of "tough" became the standard of masculinity, being applied retroactively to the slowly disappearing cattle industry, painting handy men and more rural, manual labor as an attractive setting. This is where the stereotype of pornography centering around men in unskilled labor positions entering homes of married couples and having sex with wives of more white-collar workers comes from. It as an ideal that concentrates on a physical production over a mental production. Whichever you choose is fine.
The return to a more dandy-like preference for men comes largely from the feminist movement and societal pressure on heterosexual relationships to be equal. Feminists criticized popular movies in which motorcycle drivers and cowboys-like characters open disrespected women or had multiple partners as a sign of their potency. They criticized that portraying men as doomed heroes who felt no shame in their actions or had no regrets worked as a metaphor for sexual intercourse in which males have (and should have in the prospective of the filmmakerS) a physical and psychological control of the situation in which they are unable to connect with a woman's own agency.
The fact that cowboys were also often migrant works is what developed the joke (which I used) about the abandoned pregnant mother; the trope of a ever-moving cowboy as the ultimate sex symbol clashed with the inherently derived trope of the woman who controls the household as her husband / lover travels for his physical labor.
While in the movies and novels, this walking into the sunset appears very romantic and quite erotic, in reality, the economic burdens this relationship would (and often did) convey upon the woman in the relationship caused them to work multiple jobs that did not pay well due to the requirement of flexible hours.
A good book that documents this subject of women subjected to such labor do to economic hardships created by an unequal physical and emotional relationship expectation is called Nickel and Dimed.
It's a quick read.