We get told in ways both obvious and subtle that there are certain ways of looking and being visually, that are socially acceptable, and those that are not. But if the point of all this vast Attire language is to allow, and forward expression of the person, then its vital that we be strong, and steady in our willingness to state who we are without too much alteration. Sure, we live in communities, so a certain amount of awareness is considerate, but beyond that consideration, we should be unafraid of flying our own flag, without apology or explanation.
Now, don't mistake me here, would I love us to live in a culture where the sorts of judgements we routinely make of each other carried less vitriol and consequent pain with them? Of course I would, and I do try, with only middling success to rein that tendency in when it rears its head, which is why, for example, you won't see me ever saying that I think some garment or ensemble is ugly, only that in a particular instance I don't think it does what its intended to do successfully.