This is difficult to answer without knowing your budget/preferences in footwear. I’m guessing your experience in different footwear varieties is limited due to the difficulty in finding shoes that fit correctly.

There are companies that make work boots made-to-measure for your exact feet (Whites Boots is a famous example). This is expensive. Just the fitting process itself costs 2-3 grand (at least the last time I checked), because they make a custom last (which is like a mold or model around which the boot is built) based on your feet. Then the boots themselves are $500-700 depending on materials. All in, your first pair of boots from a company from Whites might cost $3,500-$4,500 if you need a true custom shoe last built.

The upside is that boots like this last a long time, and can be repaired/recrafted as they wear down. Between resoles and rebuilds, a boot like this can last multiple years of hard work (I’ve met people who get more than 15-20 years of hard use out of a pair of Whites). Also, the boot maker can make multiple boots for you off of one last, so you don’t need to spend the custom fitting costs for subsequent pairs. This means you might be able to get two pairs of these boots upfront for ~$5k in total, and then rotate those two pairs to extend their lifespan.

The next question is: is this process cost effective for you? Three pairs of New Balances per year probably runs $400-$600. Over ten years, that is probably the same all-in cost as buying two pairs of custom, made-to-measure work boots and maintaining them with resoles/rebuilds. So even though the upfront cost is high, you may come out spending the same amount of money over a decade.

If you’re spending the same amount of money, then you should ask yourself which you would prefer: expensive, custom, heavy workboots that are durable and fit like a glove; or lightweight, disposable work shoes that do the job, but don’t last half a year before you need to break in a new pair. If you spend thousands on custom boots and then don’t like them, you’re out a LOT of money.

If you do go down the road of expensive/custom boots: Whites Boots and Franks Boots are the brands I know off the top of my head that can still do true made-to-measure. They’re both expensive, but I own two pairs of Whites that are built in their “stock” sizes and am blown away by the durability/comfort. People primarily use them for wildland firefighting and forestry, which are really tough conditions for footwear.