I didn't say it was bad. Just a shift in perception from 'something of value' to 'something to send a social signal that maybe I don't want to send'.

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).

As has been said here many times just because you don't care about your appearance doesn't mean it isn't important to your life. People will judge you negatively based on it whether you care or not.

(or replace appearance with fashion)

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.

I wasn't referring to friends, I was thinking strictly professionally. Business associates, clients, etc.