If people don't judge, why am I nearly always asked, "Why are you wearing a tie?"
I think appearances usually have only one of two aims: to conform or to stand out. There is a third outcome, that of 'no aim' - simply a 'whatever I feel like'.
I actually do think about how I'm going to dress myself depending on who I'm going to meet, mostly along the lines of "How well do I know them?", "How do I best present myself in a way that I will be accepted?"
General rule of thumb: the more ridiculous I look, the more familiar and hence comfortable I am with person(s) and/or situation.
Now this kind of makes me look shallow.
I'd like to suggest that it's not. Really.
A chef would seriously think about how food is presented, because the smell and the look of food would be in one's mind before what it actually tastes like, and we're not even going into how healthy it is or how much it costs here. So many things to present, from the very first impression. All important.
Feel free to replace "chef" and "food" with whatever you can connect with better.
So you want people to know you? What you think, feel, believe? And care?