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If it's really about comfort and ease of walking, Cole Haan hasn't been mentioned. In a lot of their shoes, in a variety of classes, they stick in that Nike Air technology or what have you for more comfort. I have one pair exactly for that reason of being able to walk all day long. I've also bought some for my dad who, through a combination of old football injuries and blood sugar related ailments, needs something that diminishes the pain in his feet and still looks professional.
 
I walk everywhere in my non-Alden pennies, but they all have those rubbery do-hickies affixed to the soles, thanks to B. Nelson's shop. Otherwise the soles get torn up too quick in this city.
Cities are tough, but I think it would take a long time to wear out a sole, and then have B Nelson replace it with a double sole, (as he does for Mac, I think). You'd be many miles down the road by the time that wore out.
 
At 5-7 miles you will be fine with leather soled, good quality business shoes. Also, after the trip they will fit like a glove. Bring alternate shoes and athletic tape for heels and soles ;)
I agree. Hopefully the shoes (and your feet) are already broken in though, so you won't need the tape.

That sounds like a lot of walking to most Americans, but it's probably typical for car-free cityfolk, who ride trains and buses and walk.
 
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