Sounds like you’re looking for boots, not shoes. I hear you, I hate how I can rarely find a good pair of shoes and then when I finally do, they wear out in 1-2 years and anything remotely similar to them has been discontinued. I hate walking through a snowbank in winter and having it get wedged around my ankles. I hate stepping in a puddle and it turns out it’s deeper than expected and your feet get soaked. Fuck shoes.

Several years ago I got a pair of Redwing 4473 boots with the zipper insert (I’m too lazy to mess with all those laces) and they’re still my primary work boots. I just had them resoled for the 2nd time and they’re in excellent shape again. Awhile back I realized that they were by far the most durable, comfortable, and all around best pieces of footwear I’ve ever worn in my life despite a complete absence of cushioning, gel insoles, foam padding, etc. So I ditched shoes altogether and just wear work boots that can be resoled. I just don’t wear the nicer pair when I’m painting, digging, mowing, etc.

They don’t make the 4473 anymore and I heard the overall quality has gone downhill but I think you still need to research the individual boot model as much as the maker because some are winners and others are lemons. For my nice not-work boots I’m trying out the Solovair crazy horse gaucho 11 eye derby boot. A local cobbler installed a side zip on them for me for $70 because again, I’m lazy and don’t like to screw with boot laces. I won’t know whether they’re worth it or not for a few more years but I like how they look and they’ve been comfy enough so far. Pair some good leather goodyear welted boots that are properly broken in with a pair of wool Darn Tough socks and you’ll never go back.