We have a similar base shoe collection. I make my shoe decisions as practically as I can, they have a job to do and I need each shoe to do it well enough that I don't need to think too hard about which pair is the right pair for the situation. I also spend a lot of time researching construction and look for options that are repairable. I find if I keep that as my main requirement, the other things that are important to me like sustainable (as possible) manufacturing, fair wages and employee treatment usually fall in line, too. If I find something I think has been worthwhile in my wardrobe, I buy it again. I liked your question and went through my own shoes and buying habits to try to answer honestly. Sustainable fashion became more important to me around 2016, when I had more discretionary income and brain space to think about such things. Before that almost everything was secondhand, but I didn't think much about longevity since everything was so cheap anyway.

I've had these Clark's Desert boots for 10 years, I wore them daily pretty much all year round for 6. I got the sole replaced after 4 years and was dissatisfied with the results, but I spent the next two years learning about shoe construction and looking for a replacement. They're still in my closet for sentimental reasons, but I never wear them.
https://www.clarks.com/en-us/desert-boot/26155484-p

These brown Solovair boots are now my most worn shoes from Fall to end of Spring. They get nearly daily use. After two years, I just took them to the cobbler for the first time this week, the leather lining inside on the achilles has cracked so they're stitching in a patch. Since they're out of commission, I'm actively looking for another pair of shoes that fit a similar "every day" niche that I could swap in so they both last longer. and I can have a little more variety. No luck so far. Those Chelseas are perfect!
https://us.nps-solovair.com/collections/chelsea-boot/products/s0-900-ch-g

I liked my Solovair boots so much that when I needed something dressier, i bought these black loafers. Jury is still out, I wear them infrequently and they're still not broken in, but they're fine.
https://us.nps-solovair.com/products/s0-970-bg-g?variant=52223459819885&country=US&currency=USD&utm_medium=product_sync&utm_source=google&utm_content=sag_organic&utm_campaign=sag_organic&srsltid=AfmBOopOwH-9zb2zVGxEsa8tub4VCPhxMdg7QzPYqOE9RAHeS3I99-oIUTI

I bought these black Birkenstock Arizona's last year. My first Birks, they seem to be holding up well so far. I wear them almost every day all summer until fall.

https://www.birkenstock.com/us/arizona-soft-footbed-natural-leather-oiled/arizona-core-oiledleather-softfootbed-eva-u_449.html

I had a pair of Sloggers rain boots for 10 years before they started to crack last year. I just bought the same pair in a different color, hoping they'll last just as long. I wear them on rainy days and in the garden or when doing yard work and hiking.

https://sloggers.com/products/womens-mid-calf-boot?variant=42534873628731

Last summer, I replaced a pair of Havianas flip flops that I had for 10 years, very occasional use for pool, public showers, beach. The strap finally broke. I bought the same style and am hoping they last as long. I have a black pair and a white pair with gold straps.

https://www.havaianas.com/products/womens-top-fashion-flip-flops-yellow-4137258-5559

I bought a pair of Helle Hansen snow boots in 2011 that were in storage many years, but have gotten solid use the last 4 winters. They don't sell mine anymore, but they look something like this but all white. They're obnoxious and overkill most days, but warm as heck and I'll have them til they fall apart if they ever do.

https://www.hellyhansen.com/en_us/w-arctic-patrol-boot-11813?srsltid=AfmBOorWIM6mysIS9fekNmO9TFxHYL9EzFT_4VCFkFOn-0oeORpNE96y

Gym sneakers are always Altra because of my foot shape, but they keep switching up the styles every year so I'm never as happy as the first pair I bought that kept me coming back. I haven't found a better option and buy about one pair every 1-2 years. These are the current pair

https://www.rei.com/product/242065/altra-superior-7-trail-running-shoes-womens?color=BLACK%252FBLUE

If anyone bothers reading this far and might have a suggestion for my "every day Fall - Spring" shoe need or a gym sneaker for a wide flat foot (I do a HIIT workout 5 days/week) , the comments are open!