Everyday Boots Recommendation

Blundstone is a great company. They're Australian so they might be hard to find, but they are super comfortable, tough, waterproof, easy to slip on and off, and are very discreet for meetings. I love my 500 series.
 
I have a pair of Maelstrom combat boots. They are very cheap in price and have held up great! They're light, really comfortable, and can be had for $40 on the auction site.
 
Check out Clarks desert boots. They're chukka style boots that come in a nice beeswax leather or other finishes such as suede.
The desert boots come with a comfortable soft crepe sole or you can go for the bushacre 2 which has a more durable sole. The leather ones are a bit stiff and uncomfortable at first but will break in and soften up to be very comfortable. It helps to work the heel area by hand.

Edit: I overlooked the part about being waterproof. You can try using the waterproof sprays for leather or a wax finish might do it
 
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Can't believe no one has mentioned White's. High ,itial cost, but rebuildable. Come in brown.

Hathorn Hi-line. Made by White's. A little cheaper, but not custom fitted. I have a pair that has been rebuilt 3 times. This is the last rebuild they'll take (the boots) 4 years of use. I wore them everyday, mud, snow, shine, mud, and more water. A little care, and they work. They are heavy though. I hiked Mt. St. Helens in them. P.S. I have 3 pairs now, they are addictive.
 
If I spent that much time on my feet each day I would find a good custom boot maker and just have them re-soled when needed. Buy two pair once you settle and rotate them.
 
I have owned more than 90% of the boots named so far and I have not owned any that were finer than Viberg. High up front cost but completely rebuildable. They offer some lighter models that may suit you better than their work type boots.
 
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