For most of my life, I have only owned one pair of black dress shoes. They all had corrected grain uppers glued on to rubber soles, and each lasted me for years and years. I wore them to school on most weekdays -- in all weather, without shoe trees, and not in a rotation of shoes. It's hard to estimate, but I must have worn each pair easily 500 times. When I replaced them, it was either due to my feet growing out of them or the upper becoming irreparably marred (from salt etc.), not because they ripped or became unglued. I now wear only Allen Edmonds dress shoes -- I'm up to six pairs, bought over the last two years or so -- and although they look much nicer than the cheapos, it's clear to me that buying $200+ shoes is not a money-saving investment. These shoes would have to last a LONG time (read:fifteen years) to be in the ballpark -- and who knows how long my adhesive construction shoes would have lasted if I had treated them with the same care that I now treat my shoes with. TL;DR: In my experience, expensive shoes aren't an "investment" in the sense that they save you money in the long-run.