I haven't read this whole thread, so if this post is awkward oh well!
But, I have the opposite problem!!! I'm actually country and I wear muck boots, ripped jeans, and whatnot to go riding, but in school I dress up in a polo, khakis/nice designer ripped jeans and somenice sneakers and a jacket and whatnot!
Everyone jokes that I would be the last person they would suspect to be country-ish in my school :p
However, there are wanna-be rednecks in my town that wear plaid shirts, jeans and construction boots and I really don't give a flying poop. They an do what they want and as long as they don't annoy me I won't bother them.