I have to wear black shoes every day, but I generally find most mens’ shoes uncomfortable. I used to have a pair that looked like dress shoes, but with a soft sole and felt like sneakers. Would really like to find something like that again, but they have to be durable too and can’t look cheap.
Nunn Bush. I have a pair that look reasonably dressy and are quite comfortable. The soles also have excellent slip-resistance on wet surfaces. Sorry I don’t know the model name/number and can’t readily provide a link with this device, but it’s easy to find them online.
My husband loves Nunn Bush, so I’ll second that. Could you get away with Danskos? I wear the clog style constantly since I have plantar fasciitis, but they’re passable with dress slacks. They have a few lace-up models too. Anyway, they are more comfortable than any sneaker I’ve owned. There’s a reason hospital workers and cooks swear by them.
If most shoes hurt your feet, I would suggest getting properly fitted for shoes. So many people ask for size 10, or whatever, because that is what they have always worn. But if you are actually a 10.5 or 11, yeah there is going to be some discomfort.
I’ve always found Rockports to be comfortable. Some look dorky, but others look just fine. I’ve looked at Nunn Bush, but have never owned a pair. I don’t wear dress shoes all that often, but I would suspect that any comfortable ones with soft soles will not be as durable as traditional dress shoes.
My “daily” dress shoes are Rockports - super comfortable, and the right amount of dressy to go with business casual, nice jeans, or a suit in a pinch. They’re just as comfortable as sneakers for the most part (and, indeed, many of them have the adidas cushioning in them). I do have two pairs that I rotate, and they generally last a couple of years each; I don’t take particularly great care of them, and I’m wearing them 6 days a week. They’re not as durable as a true dress shoe that can be re-soled and last nearly forever, but they last long enough for me to be happy with them.
Thirding Rockport. I have high arches, and most every other brand I’ve tried really just don’t fit that well. Both the Rockport sneakers and their dress shoes fit me better than everyone else’s.
Rockports are fairly comfortable and reasonably supportive but not ultra durable. You also need to be aware that not all Rockports come with the flexible sole, some have standard leather soles so look carefully at the specs. when shopping.
I’ve worn this shoe as a daily work pair (office, business casual) since 2011. They’re very comfortable and very durable, though not very formal. The first pair lasted 3 years before wearing down, and I’m still on the second pair.
If it has to look on the dressier side, spend more on a good men’s shoe like Johnson & Murphy or Allen Edmonds. You’ll spend a couple hundred bucks, but they’ll be comfortable as hell, look good, and will last forever. Shoes is one of those items where you get what you pay for.
I have to emphasize the need to get properly fitted. We have a lot of trouble with shoes in my family, because some cave-man gene resurfaced with me and I cannot buy shoes wide enough - 6E and up a full size from nominal is the best I can do. My son is a little luckier. His sister… is going to have trouble with shoes her whole life, as they do not make truly wide womens’ shoes.
Anyway, between my experience and others who kept wearing their high-school size into increasingly painful adulthood (one boss was 40 before he discovered he wore a EEE) - get a good, professional, experienced sizing and THEN start evaluating shoes for comfort.
ETA: This means NOT the tweener staff at Payless Shoes. Go to a good men’s shoe store and get the older guy to do it. Then buy at least a pair of socks or something if you’re not going to pay those prices.
If you’re buying shoes to wear to work, it helps to wear the socks you plan to wear with them when you go shoe shopping. So if you wear nylon dress socks to work but wear cotton sport socks on the weekend, wear the dress socks to the shoe shop, even if they look silly with your weekend sneakers.
Doc Martens are extremely comfortable, but tend to be heavy, and may not exactly achieve your definition of dress shoes (I wear my black Doc Martens with my Tuxedo).
In the same general price range, Rockports are nice, wear well, and I’ve found many pairs to be extremely comfortable. Friends have called them my “old man shoes”. YMMV
Johnston & Murphy are fantastic shoes. Very good looking, very comfortable. I have a pair of waterproof brown ankle boots I’ve owned for 3 years that are my daily wear. They look brand new and they look good with jeans or a suit.
They’re not inexpensive but you can expect them to last.