OK, again, as with the glasses, we come up against the problem that those actually are the most comfortable and practical shoes.
True, they've become 'hip', but if we eschew simple black plastic framed glasses and Converse All-Stars, we will be stuck with worse glasses and worse shoes.
It is quite different with some items - particularly the tight trousers depicted above. I mean who could actually wear tight trousers? Its crazy to suffer discomfort. But for things which are the best I doubt I'll give them up just because they became too hip any more than I refused to give them up when they were too un-hip. (yes, I'll admit I have been wearing black plastic glasses and converse continuously from 1976 till the present, except for occasionally veering into the gold metal-framed and boat-shoe subcultures).