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how does the red wing gentlemans' traveler hold upi in everyday use will the boot last for years
^^ I think that RM Williams Craftsman, Blaxland, or Comfort Craftsman would be better if you are wearing chinos + tie. There's a good thread on those boots in Men's Clothing.
And yet there's the question of foul weather and situational compromise. I work in a semi-formal environment that tends to be especially tolerant on foul days. This is particularly true during bad New York winters, when actually getting to the office on a snow day creates enough good will to allow for Timberlands, let alone upscale hunting boots.
I don;t know waht all that says but these boots are not dressy. Then again you spent 40 minutes explaining how your workplace allows crappy inappropriate shoes, so I don't see why you would have a problem.
long response
^^pain at the back of the foot at break in is dependent on how the boots fit. Try to tie the laces tigher around the ankle to prevent slippage.My 8138s however never gave me any trouble.
[Useful information] http://www.alden-of-carmel.com/index.cfm/shoes.htm