The faking, the peddling of something just wholly unsatisfying...  even a shop near me called 'Kitsch'...  but it's partly nostalgia, partly silliness perhaps and the realisation that you took something for granted and now it's gone: like the respectable working class; unlike the horror show freaks I saw yesterday with their cavemen features, their piercings and tattooings, their loud, brainless utterings, the lack of restraint... 
It appeals to the 'collector'.  Maybe 'collecting' is some form of psychological condition.  Buying Redwings in England of course is a bit different to buying them in the US.  I couldn't see too many of our real arseholes going in for workwear exactly, more street style so long as it requires little taste, discrimination, imagination and everyone else is in it, i.e. it's safe to be seen in.  I've never seen so much Lauren and Lacoste as during this summer. 
Gibson Gardens could give you the lowdown on this new breed of Lib-Tories we have now and the Boden crowd.  Hard to spot a genuine working class person amongst so many who are just plainly badly dressed...