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Because the series Naruto never did that with her in canon material.Kishimoto never had her wear revealing clothes till The Last.I am not cross examining mutiple verses.I know there are many fan service series having both shy and aggressive girls with huge bosom.I am just saying Naruto was overall never of that type
The Last was considered canon by Kishimotto. Meaning what ever dress she was wearing Kishi approved of it. Your whole arguement of this style not suiting shy girls is irrelevant. When there is multiple cases of shy girls wearing revealing clothese. Not sure why you would debate against something that is so simple to understand?