Augustine is, a capable person, but that also leads him to have this "I'm surrounded by idiots" mentality.
That includes the women who he thinks are just wasting time trying to get attention from men.
Many of the girls in the school are engaged, they have their future course set. So attending school is matter of formality, building network of political allies, or to look for potential husband if they haven't got fiance. Academic pursuit is not the top priority.
If anything, Alandra is probably the closest there is to his preference of "smart girl". But she doesn't stand out, and would rather choose research career than getting married, especially not to a crown prince.
In the past loop, he never loves Leticia. Their marriage is political (because he is pressed to choose a wife). Then, Leticia's act on wasting money in attempt to get his attention made him detest her more.
Isela actually falls into the category of girls he would have hated. The only things in her mind is enjoying the fact he is her lover and wants him to give her attention (and enjoy being the winner in life).
It only works because they have an enemy (Leticia) to overcome together so he overlooked it. Isela did brainwash him at their first meeting, but the magic will fade away on its own. In the end, it's his own choice to stay with her and get blinded by love.
And things aren't exactly flowery for Isela after Leticia is executed. She thought they are going to be "living happily ever after", but being a queen is a job, and people quickly points out how she lacks Leticia's manner and upbringing.