Shoes and boots are one of the few items where you have a ton of made in Canada options.
I’ve gotten pairs from a few different brands and the stand out value is the WM. Moorby line by Canada West. My set haave been durable, and look as good as boots I’ve bought at twice the price. They aren’t cheap ($300+) but they can be resoled so they should last roughly forever.
$300$375
Zowie
That’s about deadon for quality boots. I have a pair of Redwing Blacksmiths that cost about that much and have had them for 7+ years, and they were worn daily tromping through Boston for a couple of those (they are not winter boots, no fucks given) and they still look and wear amazing.
The break in though, SUCKS.
I bought a pair of Keen lace up work boots for $320 last April/May. By October I had to do a warranty claim on them because they were falling apart at the seams and leaking like crazy. Super comfy boots and in my experience their customer service has been good, but I’d happily pay a few more bucks to have something that might last a few years.