If I could find something really comfortable for less than $150, I’d be happy. Happier, yet, if I could spend less!!
Munro shoes on 6pm might be one option worth looking into. Here is a bootie that would work with both pants and black tights/skirts:
http://m.6pm.com/munro-american-grace-black-leather
A nice flat that has a built in wedge for comfort:
Do you have a “The Walking Company” store near you? If you do, it’s worth looking there…I’ve actually never bought shoes from them, but they do carry lots of comfortable brands…I also like Munro very much and another brand Rieker. I have found very comfortable boots both short & tall that I live in most of the Fall & Winter. I have had very good luck, often, just asking the clerks at my local DSW shoe wearhouse for very comfortable walking shoes or boots and I have been pleasantly surprised by their comfort level over the course of a day with a lot of walking. Not sure, but I think one pair of boots is Bandolino. Not expensive, but comfortable, imo. Just go to these stores and try shoes on…you will quickly be able to tell what’s going to be comfortable for hours of wear at a time and what is not. Good luck 
I love Munro, but I wore my cole Hahn black sneaks in suede all through my Cambridge visit. They re suede, with tiny holes, and come in red, turquoise, gray, blue, orange, etc. they look good enough to wear to any restaurant, and I walked miles a day. They also come in leather.
Did I mention that I got to airport, and sat next to a woman, who was wearing the same sneaks?
Those booties are really cute BB, but there is no way i could walk miles in them in NYC.
I went shopping today for comfortable shoes to wear on a trip I’m taking. Ugh! Trying to find shoes that are super comfortable that I would wear when I came home seemed impossible.
Came home and ordered the Cole Haans that bookworm mentioned.
deb922 or bookworm, could you provide a name/link for the Cole Haans?
Don’t think the bootie will work for me BB. Keep ‘em comin’!
This is the shoe I walked all over SF with. http://www.merrell.com/US/en/dassie-buckle/17324W.html?dwvar_17324W_color=J69076#cgid=women-featured-best-sellers-footwear&start=1 Very comfortable!
These are the shoes I ordered http://www.6pm.com/cole-haan-zerogrand-sneaker-black-black-shimmer
I ordered from Amazon because they were the same price in my size but offered free returns.
http://www.amazon.com/Cole-Haan-Zerogrand-Fashion-Sneaker/dp/B00WJBN2AS/ref=sr_1_7?s=apparel&ie=UTF8&qid=1443660164&sr=1-7&nodeID=679394011&refinements=p_89%3ACole+Haan
This is another style http://www.amazon.com/Cole-Haan-Bria-Grand-Sneaker/dp/B00MMU0NIK/ref=sr_1_9?s=apparel&ie=UTF8&qid=1443660164&sr=1-9&nodeID=679394011&refinements=p_89%3ACole+Haan
These may not be the ones bookworm mentioned, she said hers were suede. But I liked the black with pink that I ordered.
I didn’t want suede because they aren’t that practical if it rains.
Panhandlegal, is it the heel or the style (bootie) or both? Just trying to target my search. I have Munro Mary Jane style shoes with the same heel, and they are amazingly easy on the feet. They bounce off the ground like there is a set of springs embedded in the soles.
Very nice shoes, deb! Just want to ask the designers at Cole Haan one question: why did you have to ruin such a lovely shoe by putting a white sole on it?
Deb922 posted my suede shoes. Nordstrums had them on sale, but Ina few colors. Cole Hahn said they meet the price, and had 6 more colors. I got the practical black, so,I was fine. Whether suede or leather, they have a dressy look, but are super comfortable.
Yea I’m with you on the white soles. I tried them on before and rejected them because of that. But decided later I could live with the white sole. The 3rd shoe I linked, the Bria had a black sole but wasn’t as comfortable as the zero grand.
Some additional options:
http://www.6pm.com/cobb-hill-ivanka-black
http://www.6pm.com/paul-green-carolann-black-leather
http://www.6pm.com/ecco-sculptured-45-w-slip-on-coffee-coffee
http://www.6pm.com/ecco-abelone-stretch-slip-on-marine-marine-firefly-textile
http://www.6pm.com/ecco-abelone-bit-black-black
http://www.6pm.com/taryn-rose-paislee-black-soft-nappa-patent
I think the white soles are meant to capitalize on the trendy sneaker trend. It makes the shoes look more like sneakers, which is the look they seem to be going for.
^^Mathmom:
Those are cute! And look comfortable. I may have to look into getting a pair of those for myself! 
Just a word of caution on Munro shoes, and any other brands with polyurethane soles. I have a pair of Munro booties that are about 8 - 9 months old. I wore them a few times last winter, then they sat on a shoe rack until last week. The soles have disintegrated, which I didn’t notice until I saw a trail of black bits through our house. After one brief additional wearing, the soles fell apart.
Munro’s website states that PU soles absorb moisture and will crumble. Both Munro and Hotter (a UK brand I also buy) warn against storing their shoes in shoe boxes and/or poorly ventilated closets, and say the shoes should be worn regularly. My shoes weren’t kept in a humid location, but I can’t wear ankle boots in our hot climate for more than about 3 - 4 months of the year. If I had worn them they would have been subject to much higher RH outside than in our home.
nottelling, you are correct, that’s the look they are going after. Ruins the shoes for the dual use as a casual and semi-dressy option!
Silpat, interesting, thanks. My Munros are 5 years old and still look like new. I don’t wear them often. There must have been some change in the composition of the soles, because I do not recall seeing any such warnings when I got my shoes back then.
I really don’t need more shoes that look like sneakers! My problem is finding something for my wide feet - even wider now that I broke a toe! I never seem to have anything that looks good with a skirt or capris that I can walk in for long. I generally don’t like even a wedge heel though I had a great pair of closed toes sling back almost sandals I wore all summer. Great for job sites and climbing ladders, but comfortable without socks.
It is sad that some companies that start on the path towards comfy, fashionable shoes quickly reduce their efforts to making sneakers and clogs with a few “wild” styles sprinkled in.
Is anyone here following the fashion weeks? Judging by what I saw online and in the catalogs of RTW sent to me by department stores, my wallet will be safe. Only the Max Mara’s current fall collection makes me drool over some pieces.