I tried numerous brands from very low end (Kenneth Cole) to very high end (Salvatore Ferragamo) but could never find a brand that was durable or comfortable.
Then I discovered Cole Haan. I'd say they are in the mid range of price (200-250) but I've had 2 pairs now that I alternate between daily for the past year that look like new. They have Nike Air technology built into them - so they are very comfortable.
I'd suggest Cole Haan Air Rivington Wng Ox
but if that's not your style, go with a cap toe style.
Allen Edmonds. I have 3 pair as hand-me-downs from my grandpa and they are like slippers, I love when I have to wear them because they look great as well. As a topper, they're made in America.
Cheers.
I agree with Troy that Kenneth Cole and Cole Haan are two good choices. I'd further suggest going to a Macy's or another store near you and try on whatever shoes you're considering (as opposed to ordering online). Each pair (within the same manufacturer) will fit a little differently so you should walk around wearing both left/right shoes before buying, and if they're a tad snug, that's okay because leather will expand. Make sure you're wearing the same socks you intend to wear while wearing them (ie same thickness). If you'd prefer, buy the shoes online after shopping for them in person but definitely see how your feet feel in them prior to buying, and definitely give Kenneth Cole and Cole Haan consideration.
I picked up a pair of Rockports at Men's Wearhouse and they are incredibly comfortable.
Allen Edmonds is a good way to go I think with a couple of reservations:
1. Make sure you try on any style of shoe you are planning on getting and don't just assume if you are an 8 E in one style that is what you will be in another style. I just got a pair of Park Ave shoes that fit great and are comfortable. I also got a pair of a more biz causal style slip on that destroyed my feet with blisters because they did not have my size at the store and ordered them for me. So I never got to try them on. Big mistake. I think their less formal looking shoes are not made in the same place, use a different last (is that the right word?) ect.
2. If you are trying to save money, go get measured and then pick up some used one on ebay for $30-50 and take advantage of their reconditioning program. You will get a pair of brand new looking AE's for about $130 all in that are also broken in.
Personally though, I wear cowboy boots to work most days (banker/lawyer) And no dress shoe I have ever tried on is more comfortable or (in my opinion) looks better than a Tony Lama boots. Plus they are much more versatile as far as when you can wear them and (maybe best of all) will give you almost 2 inches of lift which is never a bad thing.
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.
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.
Try on a pair of Rockports and then realize why they are so pricey. Insanely comfortable. Worth it!
I second the Clark's remark... more specifically, Bostonians. They wear well and are super comfortable.
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I tried numerous brands from very low end (Kenneth Cole) to very high end (Salvatore Ferragamo) but could never find a brand that was durable or comfortable.
Then I discovered Cole Haan. I'd say they are in the mid range of price (200-250) but I've had 2 pairs now that I alternate between daily for the past year that look like new. They have Nike Air technology built into them - so they are very comfortable.
I'd suggest Cole Haan Air Rivington Wng Ox
but if that's not your style, go with a cap toe style.