Are you a giant?

I fill out a doorway real nice, that's for sure

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.

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Thank you, and yea I should have included a budget, as you said I do spend like 400 on 3 pairs of NB, and was hoping to top out at the 500 mark, but the idea of custom boots certainly aren't off the table

Oh man I feel for you my husband is a size 14 shoe and we struggle to find him proper shoes. I know he likes red wings but I’m not sure they’re made in a size 18.

You'll have to work out the details with some makers, but you could get yourself some clogs made. You'd be going well to wear through a pair of wooden soles I should think. I get mine (only 6'6", 170lb, UK size 14) from Walkley Clogs in West Yorkshire, UK (they export). They are surprisingly reasonable.

You might have a look at Wesco boots. I had a custom pair made by them ten years ago, still going strong, although I do alternate btwn them & redwings & NB, depending on what I’m doing that day..

I'm just here to upvote the White's. My father, who is over 80 and doesn't wear anything else, would tell you that you're wasting money repeatedly buying anything else. It's no joke, they are a very large investment. But one you'll never regret. Just be sure to get the custom built ones, not something "off the shelf". If you can't swing the investment at this time, that's totally understandable. But it's something well worth starting to save up for.

I like the idea for sure, is there a way to have a different (read as cheaper) person do the measuring? I can swing the price of the boots, but the measuring costs seems steep

I wish I could help with that. I know my dad originally did plaster castings, back in the day. He says they still keep them "on file". I have no idea what method they use now. Sorry I couldn't help.

you may want to check the content on r/goodyearwelt to find some high quality work boots that can be resoled. for up to 500$ you can definitely find good and heavy-duty boots, idk about sizing, though. people go for brands like Red Wing, Thorogood, JK Boots..

Unfortunately, building a made-to-measure last is an extremely rare skill these days, requiring a great deal of time, labor, and expertise. Anyone you could go to with a legitimate level of skill will likely charge in the thousands of dollars range for a custom last.

A cheaper way these companies can size larger feet is to take an existing last and build up material over it to meet your measurements. This may cost in the $50-$150 range to get sized as opposed to the thousands of dollars range. The downside is that they can only build up so much material on the last, so your feet may be too big to go with the less-expensive option.

Whichever route you end up going down, I hope you find a solution that works for you. This really is a difficult challenge to solve.