I have three pair of Doc Martens: 10-hole boots, and a pair of brown and a pair of black shoes. They all took some breaking in, but the brown ones are the most comfortable. For the first couple of weeks though…
I recently bought a pair of Aldens. Very comfortable right out of the box. I’m going to get another pair in a different style in several months.
I just bought a pair of Clarks. It was a hard choice between that and Danskos but I happened into the Clarks store having missed Dansko (I’ve heard Danskos are more comfy but I think Clarks puts more of an effort into snappy styles).
Incidentally, I consider myself to be reasonably fit and hale and hearty and all of that but I simply cannot walk around in Converse for lengthy periods of time anymore. I end up with shooting pains up the front of my leg to my knee. YMMV. They have zero arch support and cushioning. Meanwhile, the Clarks make me feel like I’m walking on a cloud. I can run, not mince, for the train now.
I didn’t even want to go near the Mephistos…they’re incredibly expensive.
Since I’m cursed with “special” feet (extra wide, high instep), I’ve always had to get the fancy shoes.
My current shoe-faves:
Josef Seibel clogs (stayed pretty for 5 years and still wearable-but-ugly now)
Keen lace-ups
Ariat clogs (current replacement for the old clogs):
http://www.ariat.com/index.aspx
Dansko, for pretty shoes
http://www.dansko.com/Home.aspx
I’ll cast another vote for Merrells. I have two pair that I wear constantly. One pair I bought for my 12-day trip to Spain, and they’re the only shoes I took. My feet were very happy.
I have bought Clarks before, and the styles are great, but I find the Merrells much more comfortable.
I’ve always heard good things about them too. I just wish they made attractive shoes 
Excellent timing!
I’m about to spend a week in New York, and one of the items on my shopping list is a new pair of black leather boots. I had never heard of Red Wings. I really like the look of these, and $175 isn’t too bad for a quality pair of boots like that.
The boots i’m currently wearing are less rugged-looking than the Red Wings. It’s a pair of ankle-high black leather side-zip boots by Ecco. I’ve had them for five years, and they’ve been extremely comfortable and durable. The sole and the outside part of the upper are both still in good shape; the only part of the boot that is on the way out is the cloth lining, which has started to rip in the right boot. They are still perfectly comfortable to wear, but the inner tends to come out a bit when i pull my foot out of the boot.
I would buy another pair without hesitation, but they don’t seem to be in the Ecco collection anymore. I think i’ll give those Red Wings a try.
Good God, what a timely thread! I just bought some shoes from one of those comfort/quality footwear stores. They’re by an outfit called Beautifeel, who specialize in very well-made, comfortable, but stylish shoes. By stylish, I mean classic style, which I love. (In fact, if I could get some shoes like I see in old movies from the late '40s, I’d be happy, but I digress.)
Check out the shoes on this page from their website. I bought the style called “Kate” in black, and they are just all kinds of awesome. Their website groups the shoes by heel height, which is convenient if you just can’t do 3" heels anymore, like me. I wore this “Kate” pair three times this last week, and they were comfy all day.
I can’t recommend them enough.
I like both the Born and Sofft brands.
oooh, I was recommended to the Beautifeel by a stylish friend but I thought the price point was a really high for my tastes. They do make some lovely shoes, though!
Yeah, the first time I saw them in the store, I fondled them longingly, but was put off by the price. However, I kept thinking about the lovely things, and Christmas gave me an excuse to get a pair. Luckily, they happened to have a sale on them the next time I visited the store. They were still costly, but much less so. I console myself with the idea that I’ll probably wear them for years.
I’m going to put a vote in for Keens. These are the ones I have and they’re heaven. I got them to wear just bumming around and they’ve morphed into my everyday/church/aerobics class shoe. I live in them. I also own a pair of Merrells and Danskos, which have both been relegated to the back of the closet.
thanks everybody! I’m going to look at all the replies tonight… just wanted to check in so no one thinks I’m going OP and run on you. Last week my office had a big meeting and they basically told us we’re not allowed to use the Internet at work, even during our breaks so I was unable to check the boards today. What a pleasant surprise seeing this quantity of replies! I knew that Dopers would come through. Thanks!
Both, but not necessarily at the same time. 
For work shoes, you really can’t beat Redwings. I have a pair of Timberlands with a Vibram sole that I want to keep forever. I bought another pair of Timberlands that were bare bones, and they aren’t nearly as good. Solid, durible, yes, but not nearly as comfortable. If you go Timberland, go for the Cadillac models.
Brainiac4 has a pair of Mephistos he swears by. Not cheap - but he’s a shoe guy.
I like Munros - they only make women’s shoes, but they make a pretty good women’s loafer. And Enzo Liberty flats. The Enzo flats are, however, not good for hours on your feet.
What got the Internet banned last week?
It’s ridiculous. I hate that kind of corporate bullshit.
If you have a spare $400, Mephisto shoes are indeed wonderful. I have a pair that are my favorites every. They’re walking shoes but look good with dress clothes, wear like iron (I’ve had them two years, wear them more often than all other shoes combined, and the soles are only now starting to show notable wear). They run about a half-size larger than marked, so I strongly recommend trying them on. Zappos does have a nice easy return program, so you can go that route with little hassle.
The most amazing thing to me about the Mephisto shoes was that they felt broken in when I first put them on. They’ve loosened a bit over the two years, but still fit about the same, which is pretty astonishing given the original fit.
If you don’t have that much to spare, Keen sandals (and I assume the shoes, but do not have first-hand evidence) are very comfortable. I have a pair that are my everyday walking shoes at Disney World.
For spending all day in, I’m a big fan of Rieker shoes. They’re German-made, and I’d never have heard of them except that there’s a German lady in a little town nearby that sells them. If you don’t want to drive to see her 
, you can also get them on Zappos.
I second: Mephistos- but buy 'em on ebay “gently used” or “never worn”.
Alden, as Johnny L.A. sez. Again, I found mine on ebay for cheap.
and Clarkes.
Keen and Merrell are nicely made and comfy, but IMHO very casual and hardly “timeless”.
More votes for Dansko and Merrell.
I wear 4 and 5 inch heels most of the time (I’m short! and nothing beats the look of a stiletto that could mame), but when my feet need a break I go right to my Danskos or Merrells.
Also my camping shoes, walking around the city shoes, etc. - either Dansko or Merrell. Cute enough, but really comfortable.