I was looking to say something similar. People are always going to judge on what you look like, for better or worse. Part of teaching kids on how to be adults is to realize that we are all different in many ways but also so very similar under the surface.
Because of this factor, I tend to dress like I own a Boat, because those assumptions are easier to deal with and dispel if I want to. They also get me preferential treatment in situations where I ought not get preferential treatment, because of the implication.
One of the kids I used to work with and I had this conversation. I helped him buy a very nice pair of slacks and two collared Polos. It freaked him out how differently he was treated by people because he was wearing a set of $50 worth of cotton.