tbh im really curious as to specifically why rook covers up his freckles. it's clearly shown to be something he just chose to start doing on his own (vil did NOT make him cover them that is misinformation!!) and ive been pondering this for a little while because rook hasn't talked about his freckles himself that much, but i believe it stems from rook just generally not seeing his own beauty in nearly the same high regard he does others
for all the preaching rook does about others' beauty, there's a specific detail - he NEVER talks about himself in the same way. confidence in his abilities sure, but even then, whenever he's directly praised for his strengths, he's shown to regularly shift it onto complimenting his peers too instead of just himself; This seems to go more beyond rook just having a strong sense of humility as well.
rook has a very apparent lack of self worth. we see this through many aspects of his character, primarily his disregard for his own livelihood and ignorance towards his safety, but this is also shown through his opinions of himself as well. furthering this point, in rook's savanaclaw portrait voiceline, he says that he had even forgotten what he looked like before he transferred, because he had always ignored his reflection in mirrors.
we also see this through the several moments where rook actively blames himself for things that are out of his control, for example in book 7, where, even after waking up crying and confused, he blames himself for forgetting those memories despite having no clue what what was going on. Or in book 6, where rook talks about dealing with persistent nightmares due to his guilt about vil's overblot, even though he knows it's extremely unlikely he could've prevented it even if he stepped in more.
i think this is also a part of what makes his and vil's relationship so special too; vil taught him how to care for himself, and in the process taught him how to love those aspects of himself as well. the story from their first year (where vil helps rook get dressed up for a neige event) shows this especially well - rook says that it was the first time he had ever felt that happy about how he looked, and from that point on began taking pride and appreciation in his appearance and care for himself.
but there'll always be a part of rook that views himself as lesser. he seems to be much more critical towards his own self, and this extends to his appearance as well. he doesn't view himself in nearly the same adoration he does the people around him, and i think him hiding his freckles may come from that.
another aspect to this is that i think it could be possible that, to him, his freckles may also serve as a reminder to who he once was. switching to pomefiore meant that rook was no longer alone. he learnt not only to care for himself, but what it was like to have friends and people who truly care for him too.
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