With regards to shoes, I currently have 1 pair of sandals which I bought in Florida in 2014, 1 pair of Sketchers which is the 2nd pair of a pair of pairs I bought for £40 a pair when they were on offer, both pairs will be replaced when this are no longer viable, 1 pair of steel toe capped work boots bought from Screwfix several years ago, a pair of Hi-tech fabric walking boots for riding my MTB on, a pair of leather walking boots, again they were on offer under £50 although the claimed Retail was £100+ & a pair of black leather shoes for hatches, matches & despatches.
Yes I do tend to buy the cheapest of anything I can find, it is only in the last 2-3 years that there has ever been any disposable income, financially we have always struggled & for many years has been my biggest worry & to some degree still is, I have no pension nestegg, I could never afford to fund it, so the future could be very bleak for us in a few years time.
That does not sound good, I have been in that position and worse, homeless with a wife and two month old when I was 18, but please do not think that people in a different position to your have no sense, or have just been lucky.