Ecco - Unbelievably comfortable

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Clarks are hands down the best shoes I've ever owned. The Unstructured collection are extremely comfortable, lighter, and more breathable than other shoes I've tried. They tend to skew a little more towards the dress-casual, but are still dressy enough for most occasions. Clarks are definitely the best <$200 shoes.
http://clarks.zappos.com/n/p/dp/34365599/c/328.html
http://clarks.zappos.com/n/p/dp/34365755/c/216.html

Cole Haan are also a good choice if you want something dressier and are willing to spend over $200/pair.

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FABI

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Allen Edmonds, Johnston & Murphy, and Cole Haan all make unbelievably comfortable and stylish shoes for around $200-$300. The price is a little steep but definitely worth the investment. Cole Haan's Nike Air collection has a Nike Air sole which makes it feel much softer than other dress shoes, while Allen Edmonds new Crosstown Collection Line is very soft and surprisingly light weight for about $199 (much cheaper than most of their shoes). I have pairs of both and couldn't be happier.

Good luck.

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Try on a pair of Rockports and then realize why they are so pricey. Insanely comfortable. Worth it!

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I second the Clark's remark... more specifically, Bostonians. They wear well and are super comfortable.

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