Honestly, never. I am a bit unobservant like that to be honest.. I remember that one of my fellow students was told she would be remembered for her always being well dressed. I never really noticed so was a bit surprised.. She looks ok, nice.. but beyond that I don't take much notice of what people wear..
Oh just to add, since this question made me think... I did an experiment when I was dating... I used always to dress up to meet people... result was positive... Then I decided I couldn't be bothered with all that - too much effort.. and the result was... still positive. It taught me something I had always thought anyway... it's the person inside the clothes that matters :)
Thank you for sharing your experience. I agree on the "it's what's inside that matters" sentiment. Although, how we look on the outside often dictates whether someone will look at what's inside as well.
This is part of a group of questions kind of all centered around the same thing- more or less, what our clothes say about us and if others even notice the messages we're trying to send. With authenticity, I was considering a friend of mine who has to have all a certain brand when creating a certain look. To that person, the outfit is not authentic if they integrate a different brand. It no longer has the same meaning. *shrugs* I think I'm more like you in that, sure, I dress "nice," when the situation calls for it, but I don't care if I fit into someone's box of authenticity or worry about what others think too much. I'm authentic to myself. My clothes aren't used symbolically to tell people anything. I just wear what I like. I guess that makes me a poser. LMAO
And I cannot disagree with any of what you said.. People do judge based on what we wear and we know there are some who DO judge if a person doesn't wear a certain brand.. I think, modestly, that I transcend clothing.. my personality kinda gets me out of lots of trouble and into lots of good things so I guess I get away with wearing naff clothes :P
I expanded a bit on it in my discussion above with DDB. I guess they'd be authentic if they were manufactured by a specific maker and designed with a purpose in mind.