most comfortable ever....way way back i had a pair of guess low cowboy boots....the heel was just perfect, the leather fab...loved them...wore them to death.

When I was in San Miguel de Allende (Mexico), I bought a pair of their famous sandals, which are designed to negotiate the town's cobblestone streets. They are attractive and wonderfully comfortable. You can buy them in the US here:

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Hmmmm, depends on the time of life and occasion. In my current casual life I am big on Nike vintage style reissues like the Pegasus 83 and Pre Montreal (trimmer and lighter than performance running shoes) and Birkenstock Gizeh. For dressier, but needing to be on my feet a lot I like SW Bacardi booties and Broadband sandals. The Broadband is rather Old Lady, but an amazingly comfortable 2-1/2 inch heel.
For a 3-week trip to China I lived in Naot Kirei mary janes. They served the purpose very well, but I can't bring myself to wear them IRL.
Back when bootcut jeans and trousers were the norm, I wore my Lucchese western boots regularly and put many miles on them in New York, London and Paris - I've never understood why footwear designed for ridin' and ropin' is so amazingly comfortable for walking all day on cement sidewalks. But they are too costumey for me with narrower pants and dresses, which I favor now. I have 3 pair and the 30+ year old ones are the most comfortable! In fact, I reorganized my closet yesterday, and finally decided they shouldn't be taking up the convenient spot they have always had in my closet. But I did move them to a high shelf that is in my direct line of sight when I open the closet door. Seeing them makes me smile!

I agree with Sterling about the Vionics. I have three pairs and will buy as many as I can find in colors that work for me. They're wide enough in the toe box to accommodate my broken toe, they are soft inside, and they have arch support right where I need it.

I just got these last week and its like walking on clouds. They aren't gear, they obs aren't for work (I work in a professional office). but I. love. these. I'd been looking for a grey sneaker for crops and to and from spin classes with leggings. I also love dansko clogs, but can wear them to work with only flared trousers. and I wouldn't have even done that a few years back, but feet getting fussier, and I will say the casualization of the office in recent years, not just my office, but where ever I have meetings, I am really surprised at what professionals show up on. Especially younger professionals. Angie's post about comfortable office foot wear was perfectly timed... though interestingly, I already have a couple that were on her list. I guess I've been on the same quest recently.

Tough question to answer because "ever" is a long time! I've been fortunate enough to own and wear many comfortable shoes/ sandals, but not all started out that way from the very first wearing -- for instance, a pair of Mary Janes from Ecco that proved brilliant for long walks while travelling began by giving me blisters!

Sandals and booties tend to be more comfortable for my particular foot. A few very comfortable options recently.

Alas, the Fitflop loafers don't work on me since I am between sizes....

Emily K--I wore through 3 pairs of those Merrills, two black and one silver. They were my main work shoes for a few years.

Besides Birks and Uggs, Melissa shoes are some of the most comfortable I've ever encountered. Granted, they are essentially jelly shoes in a more adult form, but still, heels or flats, they have the comfort thing all wrapped up.

Oh, but for more traditional shoes, Munro is outrageously comfortable. Unfortunately, their styles are sometimes somewhat lacking.

This is such a hard question, because I have a lot of very comfortable shoes. I would say my most comfortable ones in recent memory are by Think! They were comfortable even when I had plantar fasciitis. Naots took me through that time, too. Otherwise, anything by Paul Green seems to work for me, and my latest loves, a pair of Jo Ghost booties.

Pretty much all my shoes have to be comfortable. (I make a slight exception for evening-wear "sitting" shoes, though I'd rather not.) As my username would suggest, I find Danskos generally pretty comfortable for me.

Some of my most comfortable shoes ever were from Dansko's discontinued Golden Gate line of many years ago. The Lolita sandal, Jocelyn slip-on shoe, Meredith loafer, and Jette lace-up derby from this line were sooooo comfortable and supportive.

Fortunately, a few years ago, I found out that Dromedaris is the company that used to make that line of shoes for Dansko. And they still make and sell shoes that are very similar to my favorites (available pretty readily too, on Amazon, Shoebuy, etc.). I have the Dromedaris Hornbill and Falcon, which are very similar to the Dansko Jette and Jocelyn, and just as comfortable and supportive -- now my most comfortable shoes ever. I also see the Dromedaris Golden Eagle sandal which looks very similar to the Lolita; but I don't have the Golden Eagle so can't vouch for its comfort.

Admittedly, none of those styles are particularly stylish. But, especially with the Hornbill derby shoe, I can pull off a funky-fugly look.

Danskogirl - I knew the Dromedaris golden eagle is similar to the Lolita, but haven't tried it out to see if it's truly the same. It is available on shoebuy, and I have considered trying them.

My attempts at buying actual comfort brands have mostly been failures, to my surprise. But my best shoes ever are my Atelje sneaker-boots that fit my custom orthotics. The orthotic provides most of the comfort, but it's hard to find shoes with high enough volume. And my Frye-knockoff harness boots from Nordstrom BP are surprisingly good. They've become my Burning Man boots now that they're old and beat up, and I can walk around on the hard desert for hours in them. Real Fryes don't fit me as well and I'll be so sad when these finally fall apart.

Delurked: Let us know if you do ever try the Golden Eagle and if it's close enough to the Lolita in terms of comfort and support. (My Lolitas are still going strong all these years later so I don't anticipate getting the Golden Eagle.)

The most comfortable shoes ever? Hmm... there was a pair of Nike Air sports shoes that fit perfectly and felt like I was walking on a cloud. I wore them out and never found another sports shoe as good.

Then and still are my Paul Green "Ventura" booties. I love them so much! Fit like a glove and can walk in them all day. Also on this very short list, Cloud "Aline" booties. Wearing them right now. Comfort defined... just enough heel, cushioned inside (also warm), soft grippy sole.

Thank you for this thread! Such a great resource.

Alas, I have unsightly and painful bunions (surgery someday I guess...but I don't want to skip workouts for 6+ weeks!) and FitFlop sandals are my most comfortable shoes for everything but hiking (I mean, they're not alway appropriate so I can't always wear them, but they help my feet and my back and I can walk forever on the flat). Closed shoes? Mostly ouch. Sketchers and Born and the occasional Nike hurt the least.

I cannot really tell because all my shoes are really comfortable.I learned my lesson long time ago, I don't compromise on shoe comfort anymore. Especially after the nasty fall few years ago when I broke 2 bones in my right foot and was able to wear only the ugliest comfort shoes for more than a year.

My most comfortable spring/summer shoe: Franco Sarto Holts. I walked for miles and miles in Las Vegas in 100 degree heat in those shoes and had no problems whatsoever. It's a closed toe, open heeled shoe but with a little foot powder my feet always stay perfectly dry and comfy.

My most comfortable fall/winter shoe: Trotters Leana. This shoe is a loafer that came in my perfect, narrow width size.

Both shoes are flat with no/very low heels. Both were Angie recommendations.

These Eileen Fisher sport sandals.

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I love my hiking shoes. They're not stylish and by now they're all worn down (it's my only pair), but I used to wear them a LOT. I should get new ones soon, haha.

So much inspiration here, thank you all!

Other than mild PF, I don't have any foot issues, and all my shoes are comfortable or comfortable enough. But lately I've been strongly motivated to maximize comfort and ease, wherever possible.

Most comfortable casual? Croc flip flops. Most comfortable dressy? Anything by Sofft.