So far my list is: 1) Must be made of durable materials 2) Must fit comfortably 3) Manufacturer must have a reputation for good support if the boots need a tuneup (this eliminates 70% of all manufacturers sadly) 4) Should be Goodyearwelt construction 5) Specific model should be in production for a while 6) USA/Canada/Japan made gets priority, German 2nd, UK made 3rd, Indonesia/Italy 4th, China only in the under $100 range. I really don't trust the Italians to make durable items. Seen a lot of shit Italian quality at my job. I think quality is a regional thing but I don't know what parts of Italy do a good job and what parts don't. So my default is that if its made in Italy its shit quality unless there is recent evidence to show otherwise. That's why Whites, WESCO, and Dayton is on the top of my list. Unfortunately all are in the $400 range and difficult to find somewhere to try them on in my size. There is a pretty good subreddit for high end mens shoes https://www.reddit.com/r/goodyearwelt/ that I've been reading and trying to get a good idea on what to buy.
The price made me cry. I'm still crying a bit but these are by far the most comfortable thing I've ever worn. https://divisionroadinc.com/products/russell-moccasin-south-40-huntsman-vibram-olympic-black-cxl-bighorn-bison Looks like I'll be picking up so overtime shifts this month.
Depends what you use the boots for. For casual shoes I wear Vans and Converse but usually sandals. Replace them all the time. For dress, I mostly wear c. $3-500 Oxford or Derby style Boss, Cole Haan, Armani and have one pair of D&G. In my experience it is true for shoes that the more expensive ones are far more BIFL. (I have only had 2 pairs of shoes that turned out to be duds and they were both Armani but have no idea where they were made. Thankfully my shoe guy was nice about returning them.) I only have 2 pairs of "real" winter boots. (I do not wear boots with suits.) I have had both pairs for between 5 and 10 years with no issue. And they were both relatively cheap. For daily wear in messy, snowy weather I wear the 8-eye Doc Marten 1460 Greasy Booty. I cover up the stitching with black marker. :) Super durable. Easy to clean. Goodyear welt. Easy to replace the soles even though I have never had to. Good for slush and wet but I doubt they are good in really cold weather so.... For days when I am snowmobiling or the like I wear Columbia. Not that exact model but something close. If I had one complaint about those it would be that they are too hot. I usually just wear a pair of dress socks with them. And both are very reasonably priced IMO. p.s. That looks like a good reddit. Never heard of it before.