The fact that so many boys are cut that way suggests that not everyone thinks scars are gross or ugly, or that a tight cut isn't a good cut.
Ideally, we should all be able to choose the style we want for ourselves, when we are old enough to make an informed decision (when starting school, or age of reason, or age of puberty, whenever). But, as we know, there is often a pressing medical or other need that arises before then.