Exactly, I remember one day throwing out (to good will) 20+ industry shirts, from events, vendors, prizes etc... because I reached an age where the social value wasn't there anymore, infact it became prohibiting towards being taken serious.

I look at the young guys I work with now getting all excited about vendor gear, smile, and reminisce about being the same age, but to me shirts are worthless (and as noted a stigma in some situations).

Those people who judge you negatively are not going to be good friends - at best they would be some sort of aquaintance. Therefore, whether they judged you negatively or not is not going to matter to you in the least.

Unless of course that person is someone of authority over you - then you are screwd.