Thought I’d share a few of my favorite stories from my favorite themes - haircuts, masculinization, personality change, cleancut conservative transformations. Please post your suggestions as well!
Change-Up Chop Shop: Colt
The Bad Seed
Titan’s entire archive
So this might not fit exactly into the themes you described, but if you enjoy preppy clothing and clean-cut grooming, then you may enjoy Jaybird’s Floor 6 series.
It’s one of my favorites!
There’s also Barber’s Choice; I liked this series until he went with a nerd option. He never picked it up again, but it’s really well written.