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I have the same problem.
Hard to find something that looks Ok with Dockers.
I find myself commuting with my work shoes.
Bad idea I know. 35 miles each way in Dallas/Ft Worth area.

The shoes I wear seem pretty well made.
Sketchers work series.
They make a chukka version but I can't find them anywhere locally to try and I'm really picky.

I tried on a pair of the Chippewa boots and found them kind of stiff (they were new) and restrictive for ankle movement. Kind of tight on my big calves as well. Very well made though. If I rode an Indian I'd have to make them work just because.

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