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^ I love the look of converse but man they kill my feet. I would use inserts or find another brand. I tried some canvas court shoes by new balance that were more comfortable but less colorful.
http://www.amazon.com/gp/aw/d/.....38;pi=SL75
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Cons hurt my feet, too, because I can't wear absolutely flat shoes very comfortably. So I got the mini-wedge Cons that Angie has, and they are great for me! Solves the problem completely.
I adore insoles, but I also worked my way through a bunch of brands before I found the right ones for each of my shoes (yes, my preferred insoles depend on the shoe I pop them into). My cons are probably my most comfy shoe at this point.
Where do your feet typically hurt? Maybe the forum's collective wisdom can help.
How about another classic, PF Flyers? They get rave reviews on Zappos and are a bit wider than Converse plus have support. I haven't tried them yet myself, as I already have two pairs of canvas sneaker type shoes, but they're on my *someday* list.
I have a pair of red PF Flyers which are just fantastically comfy! They have the classic look of a Converse but such cushioned soles! Highly recommended!