I've just been through the boot-buying process, as it happens. For me it came down to the Red Wing Beckmans and the Wolverine Thousand Mile boots. I knew Red Wings had a great reputation for quality and durability - provided you can make it through the arduous breaking-in process. The Wolverines I didn't know much about when I started looking.

Whilst trying on the Wolverines I found them to be great-looking and also comfortable, although I didn't care for the smooth leather sole that I knew would slip on snow and ice (which we get a lot of here). I liked the commando sole on the Red Wings, but during the trying-on phase I couldn't find a size that was even close to comfortable. The nice lady at the shop said "oh yes, you will probably have blisters for the first few weeks", to which I said "balls to that" and bought the Wolverines. Then I had my shoe guy put on a commando lug sole protector, which has upped the grip tremendously. The result looks like this:



After a few days of wearing they're getting broken in nicely and are very comfortable. They're also great-looking, I think. The leather is Horween, which I suppose makes this post somewhat watch-related in a way...