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I've been wearing AlpineStars Web boots through winter (down to -5F on the freeway) and in the wetter days during the fall - they've been pretty good:

http://www.alpinestars.com/Web_Goretex_Boot/pd/np/110/p/233507.html

I have thin calves, knobbly ankles and narrow feet and I have no complaints - but try them on rather than order them from a catalogue - they will likely be too tight if you order your usual size in them.
 

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Oh yeah - they're snug at the top around the calf and they're alright for walking a couple of miles, although I wouldn't want to be pushing a bike that far in them.



I usually get brutal blisters from new boots, but these have been good, even on uneven ground out in the country. They are a little stiff at first, but they do wear in - easily enough movement to operate the shifter, even on a Guzzi.



If you're willing to go with leather, then Red Wing 980s - you can walk all day in those and they're lace ups so no worries with the calf thing.

 
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