Unfortunately, it costs $400+ these days to get quality shoes. It’s possible to find cheaper examples, but well made durable leather shoes are expensive if you buy them new.

We don't need to go back to the 1930s though. I have two pairs of leather winter boots that have lasted for a very long time now. How long these last obviously will depend on actual usage. I.e. keep in mind that these aren't work boots on a construction site. Just regular full leather winter boots for a HN type dude that drove to the train station and then walked to the office etc. plus some use for going on winter walks, going out for groceries, weekend activities etc.

One pair, $230, made in USA. Just looked it up, are now 10 years old. Perfectly fine and at this rate will last another 10, then be resoled and last another 20. These cost $440 now.

The other, which I used more often actually, made in I don't know where, are now almost 20 years old and still perfectly fine as well, tho the outsoles will need work soon.

I basically switch between the two whenever I need to wear some winter boots, except for when it's super cold, then I take out the Baffins, which are the only boots that have kept my feet warm no matter what.

In the same timeframe I've run through regular sneakers of the ~$50 kind from Costco about once per year (and I also keep 2 pairs around so I never have the same ones on two days in a row)

Rancourt starts around $200. Their styles lean casual, and their dressier options (and certainly their boots) cost more, but the construction and materials are really good.

Rancourt does make nice shoes for under $400, and so does Red Wing. Meermins are a Spanish brand you can get for under $400. Aside from that, it’s $400+ for Grant Stones and $600+ for Aldens, and even higher for Viberg, Edward Green, etc.