I am picky about shoes, but I’ve had a lot of luck finding cute, comfortable shoes. I like Fly London, Jambu and Charleston Shoe Company. I also wear Birkenstocks and Frye boots a lot. Tom’s wedge shoes/ankle boots are cute and comfortable. I do pretty well with flats (Tieks are my favorite) but not day after day.
When you guys talk about “comfortable for everyday” are you talking about just general walking (grocery store, errands, to / from work) or are you talking about sustained walking, such as being a tourist in a city? I guess I haven’t found normal “fashion flats” (Tory Burch, Kate Spade, Cole-Haan, Stuart Weitzman, etc) to be problematic for everyday run-around-town wearing. Or even ballet flats or penny loafers with little support. They wouldn’t be my choice for actively touring a city for 8 hours straight but how often am I doing that!
I do find as I get older my feet swell on flights. For the day trip I took earlier this week, I wore sandals on the plane and switched to closed toe Ferragamo heels at my destination. I think maybe 1.5 inch and a fairly chunky heel. I just don’t see a lot of heel-heels in my business settings any more. When they are, they’re trotted out by young chickies. Business casual rules the day and that means flats, boots, penny loafers. Or maybe wedges if want a lift.
Living in a large city, I walk everywhere daily (most people don’t own cars, just rent for trips out of time), so for me it’s sustained walking. V
I have a couple of styles of Aerosoles I can wear all day. Cute. Absolutely can use them all day walking in a city. And yes, I had prior problems with the ball of my foot (and have experienced plantar fascitis, back in the past, after some cheap shoes.)
Not the trendy, strappy, date stuff for an hour or two. I’m talking low wedge pumps or rubber soled loafers. I personally don’t like ortho looking shoes. I understand the pain though, and how some will need them.
I have feet like lookingforward. In cute flats with nothing but a slip of leather between me and the ground, if I am standing at all for a total of more than an hour, the balls of my feet hurt, the heels hurt-the arch hurts. No support, no padding. For work, when i am up and down, walking around the building, etc. some of the shoes mentioned above work just fine. For walking all day, I wear Sketchers sneakers with memory foam, or Easy Spirit Anti-gravity or 360 styles.
""Not the trendy, strappy, date stuff for an hour or two. I’m talking low wedge pumps or rubber soled loafers. "
I don’t do trendy, strappy either - especially with a high instep! The nice thing is that I can even wear sandals with my clients (I resisted for a while but they all wear them and the old taboo is now gone). I remember years and years ago brouhahahas in my office dress code about closed toe sling backs being inappropriate. Those days are long gone!
Gone are the days of commuting on Metro North in high heels, 8 1/2 mos. pregnant…aah!
Pizzagirl, I swear my CEP compression calf sleeves prevent the swelling during long flights. Yes, they look dorky, but I’ll take dorky over swollen! 
My commute involves a hilly 2-3 mile walk RT. I hate to change into “office shoes” - I just wear shoes in which I can walk this distance comfortably: Tod’s wedgers, Paul Green oxfords, JC boots, or the like. I feel both comfy and stylish. B-)
So, what are comfortable walking boots, priced mid-range? Stylish. Leather. Other than my beloved Uggs, which need a stretch to be seen as “uptown.”
My all time favorite boots for actual comfort are these http://www.ariat.com/HRTG_III_ZIP_W_FOO.html?dwvar_HRTG__III__ZIP__W__FOO_color=CHOCOLATE#start=1
I’ve mentioned them in several threads. I have several other Ariat boots, all of which are very very comfy, but these are my tippy top favorite. I’ve walked over European cobblestone streets, across muddy fields and also worn them to nice dinners and such. They are cute under pants, with a skirt and with leggings. They last forever. The brand is a working boot - yup, your meant to muck around in stables with many of their shoes - so they are built for function and comfort.
I also own two pairs of these http://www.ariat.com/YORK_W_FOO.html
Again, amazingly comfortable. I can wear walk in them all day without a twinge or pinch or singe. They are more stylish than the paddock boot but also somewhat more limiting for travel.
Ariat or the softer Frye boots.
@dietz199
The Ariat logo looks like a biohazard symbol!
You didn’t switch to sneakers when you left the office?
“The Ariat logo looks like a biohazard symbol!”
Maybe because the brand is worn by horse owners to clean the stables. 
Those are great boots, dietz.
@GMTplus7 LOL! I guess it does. Goes to prove yet again I have absolutely no observational skills when it comes to labels on clothing. It’s all about the comfort. (no - I wouldn’t wear shorty shorts to dinner, not now and not when I had the bumpkins that could justify such a move).
Whenever I try on clothing I put on the item or outfit while facing away from the dressing room mirror. If it is not completely comfortable it doesn’t matter how it looks, it won’t be worn and therefor not purchased.
I need to get a pair of three inch heels like the female lead in the new Jurassic Park movie. She spent much of the movie running away from dinosaurs on them. She was quite fast, and it was very impressive. Who would think, high heel shoes working like jogging shoes?
Hahaha, I just want to say this thread came back to bite me in the butt!
It was 90 degrees here today, heat advisory, etc. We went to go pick up S’s new car from the dealership. We had already negotiated so we were just going to go sign the papers and drive it home. D had on a Lululemon type athletic top and short denim shorts. I suggested to her she might want something different - just a t-shirt - but she didn’t want to, and it was so hot. Anyway, long story short, on the spur of the moment we decided to leave the guys at the dealership to finish the paperwork and go visit my sister’s family who lived nearby. Turns out they were going out to dinner and invited us to join them :-). It was a casual Italian restaurant and so she was ok, but I couldn’t help but think of this thread! Busted!
^^^ Confessions are good for the soul Thanks for sharing that story.
Danskos changed in 2008. Prior to that time, Danskos were manufactured by a company called Sanita. When that relationship ended, Dansko started manufacturing its shoes in China. Sanita continued manufacturing the shoe it had manufactured for Dansko, but the Sanita name on it. The way you can tell which one made your shoe is to look at the sole of the shoe. If the shoes were made prior to 2008, you’ll see a patent number on the sole and that tells you Sanita manufactured the shoe. If there’s no patent number, that means you have a redesigned Dansko manufactured after its split from Sanita.
Oddly, I can wear Dansko sandals, but not any other kind of Dansko shoe.
For walking, my preferred shoes are Clarks…I have a couple of pairs of them that I can walk in for hours…and hours. One is pretty flat. The other has a slightly raised heel. Both “cute black shoes”. Comfortable, and soft soled.
I don’t wear heels…much. But I have two pair I keep just in case…black leather, and black patent leather.
I also have several pairs of Cole Haan shoes with the Nike Air insole that are to die for comfortable. And my ballerina flats are Cole Haan as well.