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Yeah, complicated feelings here. I was involved with a big museum project dealing with octogenarians and "outrageous" fashion. After the whole thing unfolded I was left with a few unpalatable senses: (a) we can make it OK to be old old old as long as you have a lot of wealth and you can buy and wear astonishing clothes; (b) there's something patronizing about the whole "look you're old and you can still be the darling of cool people!" thing; and (c) it's still all about having a lot of money for clothes, so in the end, how transgressive is this really. It's just the fashion world getting bored, and saying "what haven't we done yet?" "Old!"
Any time I see 'cool' old people stories I think of Grandpa Simpson: 'I am disgusted with the way old people are depicted on television. We are not all vibrant, fun-loving sex maniacs. Many of us are bitter, resentful individuals who remember the good old days when entertainment was bland and inoffensive.'
Maybe people are not quite so bitter as Abe but these stories do sort of say if you're not keeping up with the kids then you are lacking in some way.