I always feel that people judge you differently once they find out more about you. Like, "Yes, I paid $500 for my hunt coat and my horse was bought for 15,000" is going to make people expect different things from you that "My friend gave my her old hunt coat and my horse was bought at an auction". The funny thing is, I've seen the "auction horse" beat the expensive horse at a show. For some reason the cost of something not only says something about your status, but what people expect from you. I think it is great that you can dress up in cute clothing (both at the barn and away from it) as well as have nice hair/make up and be ok with it. I do agree that people expect you to not wear makeup/look nice at the barn and judge you for it, but I think as long as you can ride and don't act "girly" (aka not wanting to scoop poop because it'll ruin your outfit or not wanting to groom because you don't want horse hair) then I don't see any reason for looking cute.
Plus you know you'll always look good should anyone take pictures. ;)
~He knows when you're happy
~He knows when you're comfortable
~And he always knows when you have carrots.