If you’re in Australia, RM Williams is probably the highest quality domestically produced Chelsea boot. They can be resoled almost indefinitely, and they can even replace the elastic sides if they get worn out.

If you need ankle support, you want THICK leather and a high shaft (8” or more). Bootmakers like Nicks, Whites, Drew’s, JK, and Franks all fit the bill. Their leathers are so thick that boot making machines can’t work the leather, and are therefore made by hand.

I own multiple pairs from the makers above due to crappy ankles and the need for serious arch support. No other boots come close, and I’ve work a lot of different boots before finding these guys. They suck to break in, but they’re super durable, incredibly supportive, and almost infinitely repairable.

Among them, Nicks is probably my overall favorite, but you can’t go wrong with any of them.

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.

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.

Believe me when I tell you that this isn’t like other wools. I have worn a large variety of woolens over the years (Filson, Pendleton, Big Bill, etc), and this fabric is significantly better. The labor intensive construction adds another layer of cost. Just because it isn’t worth it to you doesn’t mean that the people who buy it are “getting screwed.” If anything, they are choosing a manufacturer with next to nothing in terms of marketing or brand premium.

Dude, you guys can buy Lodenwalker wool garments over there. Weatherwool is awesome, but Lodenwalker has been making their stuff for nearly 600 years!

Happy to help. I really am surprised to see so many negative comments from people who are ignorant in regards to high end wool products.

Jacquard-woven wool is cleaned in the same manner as melton wool/mackinaw wool. Use a garment brush to remove dirt, dust, etc. Wool fibers don’t hold onto messes the same way that cotton and synthetics do, so the brush truly does remove most messes, even messes that would require laundering with a cotton or synthetic garment. I have inadvertently spilled wax on my wool garments, only to remove the mess completely with a brush after it cooled. Try doing that with cotton or polyester!

Pure wool doesn’t hold onto odors either. And while it does smell when wet, the scent goes away when dry. This means that you don’t need to worry about dry cleaning very often (you don’t want to launder this sort of wool in your washing machine unless you are deliberately attempting to re-shape the fabric). I have owned wool garments that were dry cleaned once per year despite daily wear in a variety of hot and cool conditions. Even then, the dry cleaning wasn’t truly necessary. I just did it because I had access to really cheap dry cleaning at the time.

For more-detailed cleaning guides, YouTube is your friend. But at the end of the day, pure wool is incredibly low maintenance unless you are up to your arms in blood, grease, or bodily fluids. These messes can be removed as well with a relatively low effort, but will probably stain the fabric. If you are worried about stains, definitely go with dark colors.

I own the Stormy Kromer wool mackinaw that goes for ~$330. It is excellent. Works in a variety of conditions. Just for the hell of it I dunked it in water for five minutes and then wore it for an hour in 5 degree Fahrenheit weather with only a thin base layer underneath. I didn’t get cold. Pure wool does have the type of temperature range that weatherwool describes. If you’re willing to go with a wool/synthetic blend, Duluth Trading makes stuff for an even better price.

All this being said, I am currently sewing a jacket from weatherwool’s fabric. The fabric blows the mackinaw wool out of the water. It’s soft enough to be against my sensitive skin without a base layer. I guarantee you that the people bashing the weatherwool‘s price have never felt the fabric in their hands. The people with whom I’ve shared the fabric thought it was a soft cotton fleece.

I am also sewing the jacket with the construction methods used by wearherwool. It’s a PITA. Slotted buttons, heavily reinforced seams, bonded nylon thread, no cotton whatsoever, etc. Its very labor intensive to build. I have a hard time believing that weatherwool’s prices allow them to earn a significant net margin.

TL;DR: the wearherwool will only be worth it to you if you want the absolute best wool fabric garment. But the people bashing the price have zero experience with the product.

Welcome! I was once stationed in Arizona but am from Wisconsin, so I think I can speak to this:

1. High quality winter coat. Lots of great options in this department, but if you want something to truly last for life, heavyweight wool will be the best. Synthetics and goose down are awesome, but they both lose more of their insulating properties over time. Personally speaking, I have met more than one old timer who still wears the same Mackinaw wool coat they bought 30-40 years ago. A few different companies make this style of coat, and the ones I know of are Filson (the original/most options), Johnson Woolen Mills (made in USA/comes with a hood), and Stormy Kromer (best price/made in USA). Mine comes from Stormy Kromer, and got it at the factory where it’s made in Michigan for $330.

2. Winter boots (preferably Pac Boots). Sorels are well known, but for a little more money, you can get much better quality/comfort/durability with Schnees. Modern Sorel is basically a fashion brand these days, but Schnees still makes them geared for the outdoors. They will even rebuild them for a fee you when you wear down the outsoles too much. Whether you’re shoveling snow, ice fishing, or snowmobiling, these will keep your feet warm.

3. Thick, knee high wool socks to wear in your boots. My preference is Darn Tough due to their quality and ridiculously good warranty.