Thanks for everyones replies- its crazy what some of you have to deal with!
I chose to not ride at an expensive barn as 1) I am a college student, therefor funds are limited. And 2) I was concerned that it would be focused on spending money as a means to show off.
Apparently, no matter where you go people are going to have different opinions on what you do. I buy quality, girly things because I like to dress as a representation of how I feel. I don't buy the most expensive things, but always keep an eye on trends and adjust to the ones I like accordingly.(expensive and fashion don't always go hand-in-hand) I love the horses I ride and the instructor I work with, and am learning tons and progressing SO much- I think I just need to grow a pair and accept the fact that people will judge me for whatever they feel like- weather I am at the rustic, new england farm or the preppy, pricey barn. Although It drives me up a wall that not everyone is open minded...lol