I have mixed feeling about this. Though shaming is a big part of this game, the MC's goal is still to improve these "young women in trouble." He considers himself to be doing a good thing, despite making a deal with the devil. Merely "sluttifying" them may be popular with the backers, but I don't think the MC would have that goal.
In contrast, look at the school in Glamour. That one actually has the goal of corrupting thing students and making them more vulnerable to manipulation. The goal is to break them so they can be used as little more than sex slaves. I can imagine the skimpier skirts in Glamour would be in line with the school's.
Yeah, I think, I know, what you mean, but there are already some approaches in game, that might in progression of the story lead at least girls nude at class without “sluttifying” the girls. There is:
the drug problem => might need stricter uniform rules, so girls can't hide things, so there are less body inspections needed
Emilies nudist story => as the headmaster showed with Sally already to Emily, there should be possibilities to allow nudists to perform their way of life at the beach => why not expand this to the school ground (not mandatory) => dress code = uniform or nude. Interesting regarding this is, that
Underwear shortage => might already lead to girls having less white underwear => and might be expanded to the other clothes
Changs formula might get into the drink water of the school and lead for all uniforms to dissolve. As it is inacceptable according to the rules for the students to wear anything different from school uniform and white underwear, they have to come nude to class. In addition: new uniforms could be available soon, but only short uniforms.
Additionally in the world of the headmaster nudity seems to be far more accepted as in our current world for many people. Despite the authoritanism, it has in this regard also something from a mostly female hippie community. And I think, the story heads more and more in this nudity-acceptance direction, as there are more and more scenes like the football scenes, where the girls get at least partly used to the concept, as long as they are among themselves (and the headmaster). With the story evolving, I think, the headmaster will find some way to get rid of Jimmy (alcohol-rehab?), Wilson (heart problems?) and Mykock (either jail or blackmail?), so that you finally might be the only man on the campus, if nudism (as rule, or as free choice beneath wearing uniform) might be introduced. But this is just guessing. I’m quite curious about how Priti’s story evolves. Because her uniform change seems to me just another step in this direction.