Formal dress, for a fundraiser ball. Can you NEVER wear that dress a second time? Or how many years before it's not totally crude to wear it again?
(Question is supposed to say "How long before you can wear that fancy and distinctive dress again to a fundraiser ball with mostly the same people")
I'm pulling this answer out the air, but I don't think it's so much time as it is consecutive use. Wear a minimum of three separate outfits before rotating. Can you imagine wearing the same very distinctive outfit (classy or otherwise) to a yearly party five years back to back? Or a formal weekly event five times back to back? If it's a totally different crowd, sure, but same crowd, no way.
People who truly don't give a rats ass about what others think of them can wear Daffy Duck pajamas--and they'll be judged accordingly. Most people, I highly suspect, does have a place inside themselves that appreciates the value of positive perception, despite their cries for not giving a shit--deny that all they might, and I'll maintain my doubt and continue to think they do care, and care not they may insist, I don't buy it.
Of course, there are a couple groups that actually don't care, but the more dignified wouldn't let what they lack influence good judgement.