Pros

No strenuous break-in period

Water-resistant leather dries in minutes

Sturdy outsole offers excellent traction

Looks great in a variety of settings

Pull tabs make it easy to put on and take off

Cons

May scuff, but easy to clean with a damp cloth

The iconic Blundstone #585 still reigns supreme for its comfort, durability, and style. Part Chelsea boot, part work boot, its leather feels soft with a pre-distressed texture, while inside is cushy and snug from the moment you put it on. We didn’t feel any tightness or have to wait a couple of wears for it to mold to our feet. Our editor Tim Kohut wears it at his standing desk for seven hours straight, and his feet never give in or develop blisters. He even took it on a weekend hike and felt comfortable the whole way, hills, dips, and all. The pull tabs also make it easy to slide your foot in and out.

I’ve worn warmer boots in my testing, but they were much bulkier. This pair has a lighter, slimmer build, yet works for general fall and winter gear.…