There is a notion of Middle Class Respectability. This notion is important to most members of my (your?) class. It can be put aside by highly-committed partisans who are intensely in favor of Trump (and who therefore don’t sweat negative information about him), but not by most people.
I have said before, in a line that I quite like, that Donald Trump is gloriously unburdened by respectability. Respectability is both a blessing and a curse.
Respectability, obviously, grants you some respect; you behave properly, according to the code of the class, and therefore are considered a member in good standing of that class.
But it is also very limiting. Many people will point out that GOP/RINO “pussies” will buckle and apologize at the first dirty look from a member of the liberal establishment.
That is the downside of respectability — people are afraid to lose it, and will quickly apologize when The Mob threatens to withdraw respectability from them.
And in America 2015, public respectability is granted by — controlled by — the college-educated upper-middle-class Media Class which controls most everything related to morals and manners.
The fact that Trump is gloriously unburdened by respectability makes him willing/able to say things that no Respectability-Craving politician ever could, like that yes, we need a border wall, and yes, we are permitted to, and should, be outraged by foreign criminals murdering Americans who are permitted to be here by Democratic mayors and presidents.
But the downside of his contempt for respectability is that he will obliviously trample things that are very important to the people whose support he will ultimately need, if he wants to do more than blow hot air.
Whether or not Trump thinks that upper middle class suburban Republicans are silly or not, whether or not he thinks they’re “losers” or not for owning only two cars, he will need that one third of the party that is currently dead-set against him.
And while Trump seems to either have a problem with women (how long did he spend attacking Megyn Kelly, versus how long did he spend attacking Chris Wallace?) or is simply unburdened by the Middle Class Respectability code of gallantry towards women, It is making a very large and influential block of people absolutely disgusted by him, repelled by him not a political level (which could always later be finessed or papered over) but on a personal level (which can never be repaired).
I would venture to say he can’t stop — I would venture to say that in Trump’s world of yes-men and eternal entitlement, calling a woman ugly is just sort of something he casually does, and, like a high school super-jock who’s always been protected from the consequences of his actions, he just has never had reason to internalize that dismissing a woman as Sexually Not Up to My High Standards as an opening gambit in conversation is socially disfavored.