Dear Vogue,
I think that you are reading to much into what people are saying/ writing. While I do not agree with Rap music, that is your choice.
As for colorful skirts/ maxi dresses. There is nothing wrong with color, you do not have to be a bais yaakov girl, if you do not want to be there are plenty of frum girls who are not bais yaakov and wear color. Do not let anyone impose there hashkafic values on you. Hashkafa is really a thought process, it is how you view things in light of the Torah.
There is a great blog out there called praticalhalacha its done through wordpress. It might give you some insight into different ideas.
I think that WIY-really disagrees with rap music in general.
An idea that might help you here is if you feel the need to express your bottled up emotions start writing. That will also help you decompress and then afterwards you can look back at what you wrote and see where you have grown.
Good Luck with everything.