~~$300~~
$375
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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.
I have a pair of WM Moorby boots from Great West, they are excellent, probably 5 years old and still look and feel great. Highly recommend if you can afford them.
Not running shoes thought. I only found two candian companies and one of them have too expensive shoes