Well, I rewatched the videos just to make sure I wasn't imagining things when I saw your comment. You have made up your mind that the videos are insulting to brunettes when there is no such thing depicted in the videos. In fact, in the IKYWT video, you can hardly tell the hair color of the girl (or girls). Looks pink…

You need to rewatch those vids. In I Knew You Were Trouble, the boyfriend just makes out with some random girls all on his own. There is no indication that the girls are trying to "steal him" from Taylor or that they are even aware that he has a girlfriend. In We are Never Ever … there is no competition because Taylor…

There is nothing "bad" about the other brunettes in the videos, though. Well, except the brunette Taylor in You Belong with Me, who is portrayed as the shallow popular girl. The other brunettes are not portrayed as "bad". They are just the competing love interest. It is common in movies and TV to cast the competing…

A lot of the hate Taylor Swift gets is misdirected hate towards "skinny pretty girls."

You should look up that picture of 12 year-old Taylor Swift with cornrows and crooked teeth. I can see THAT Taylor having crushes on boys and being ignored.

That's probably just for contrast though. Especially in the "You Belong with Me" video, since she was playing both characters.