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I would look at Keen brand boots and shoes. It's impossible to name a particular model that I think would be ideal for you, but in general their product line seems in line with your criteria.
 

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Allen Edmonds has a weather resistant version of their Higgins Mill boot design that can frequently be found of sale for something under $300. It looks good, is well made, water resistant and is fitted with a Dainite sole, providing pretty good traction. If you are going to depend on a single boot/shoe, this might just be your best option. ;)
 

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I have been wearing Gokey oxfords for the past year. Soon to have the soles replaced with vibram mini lug soles but they are functional, sturdy and wear well. Gokey was sold by Orvis to a private entity a couple of years ago and the shoe redesigned to accomodate an orthotic if you wish. It's my go to shoe for everyday wear in cooler/cold weather.
 
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