Jacob has more of an advantage than his father because of Eton and because his father had climbed the greasy pole before him, but his background is exactly the type that "We came over with William the Conqueror" aristocrats look down on. He has more in common with Otto English's mother than he would probably like to admit. Just like her, he is a caricature of the British upper classes, not the real deal.
Plus, of course, he has risen to the top because the people in his constituency vote for him.
But the previous consituency (Wansdyke) that covered a similar area was Labour from 1997 and until 2010 (the Blair/Brown years), when it was abolished and replaced by North East Somerset, at which point Rees-Mogg won it for the Tories. Prior to 1997 it was historically Tory.
So, we might conclude that it's a moderate Tory seat that doesn't mind going Labour provided its moderate Labour and not Corbynite-type Labour. It's certainly not populated by bunch of dyed-in-the-wool intransigent Tories, so there's every chance Rees-Mogg might have lost if the constituency didn't like him.
Interesting, Rees-Mogg is an arch-Brexiteer but his constituency only very narrowly voted in favour of Brexit (51%), so perhaps they like him and not just the party. Although the Labour and Lib Dem opponents split the Remain vote 50/50, which certainly helped him.
doing a good job should be more important than how one appears, however people's tend not to be rational.
Catholics?
>The remaining Jacob Rees-Moggs of the UK stick out like sore thumbs and are almost caricatures
Then why has he risen to the top? The common people are not just itching for a caricature of an aristocrat to lead them, he represents people that are similar to him.