I used to do it quite a bit up until about two years ago, more or less shortly after I finished high school. I only really owned four sets of shoes at most given times back then, black leather for school and other formal occasions, slipper kind of things which I wore around the house, soccer boots; and a set of joggers. Not because we didn't have money or anything, on the contrary my mum would have been ecstatic if I asked to go shopping for shoes instead of being dragged about. But they were just shoes and for non demanding occasions all I saw the need for in a shoe was something relatively comfortable and innocuous. The idea of being at all judged on my shoes never perturbed me, the sort of people who might reach any sort of opinion based on their shoes would be superficial dolts whose respect wasn't worth chasing.
Then I got a job, quite a high paying one and whilst saving is good I was literally spending money on nothing. One Friday afternoon having effectively earned $1100 that week I went to Parramatta Westfield wanting to get some kind of indulgence for my marathon of pallet stacking I had done. I shopped for two hours and went home with a packet of chips and phone credit. Eventually I started getting upgrading the fashion I had slightly, and then more than slightly and along with it I came to care more concern about fashion. Now I own so many sets of casual shoes I would never wear joggers casually, if for no other reason, for fear of the casual shoes not getting use. I'm not proud of it though, I respect the highschool me more than the current one in this regard and am more inclined to make a positive judgement on the jogger wearer than the chuck wearer.