Those with foot/ankle issues, what do you wear when you wear a dress/skirt?

I have dressy flat shoes. They are out there. Go to a good, high end shoe store and tell them what you need.

I feel your pain! I had a bad lisfranc fracture to my right foot a couple of years ago, so I am limited in the way of dress shoes as well. I wear orthotics in my walking shoes, but they do not fit my dress shoes.

I am in south Florida, so most of the year I can wear Orthoheel sandals with dresses. I can go short periods of time when I don't need to walk, in lower heel Clarks dressy sandals. Sometimes, on a cooler day, I match tights close to the color of the shoe to take attention away from my feet, and that works with dresses.

http://www.zappos.com/womens-orthotic-friendly-shoes~u Maybe something here would work for you?

I just bought some Pikolinas boots from Online Shoes. They have removable insoles that will allow you to put your orthotics in. They're really beautiful boots. I have a much harder time finding shoes in the summer that are cute enough to wear with skirts.

I've had four foot surgeries, so I empathize. I still am somewhat limited in my choices. I agree with happy housewife about dressy flats.

I found a Munro (excellent brand for comfort) style that was perfect for me a few years ago, and I'm glad that I bought it in several colors. It's basically a loafer but with beautiful leather and a nice touch of croco.

Thanks so much for your nice answers!

I have gone to many good stores and tried on a gazillion pairs of dressier flats and even ones with a very low wedge. None have worked so far. If they fit have decent, then the orthotic lifts the foot up, such that it makes the shoe flop and slip out of the heel. I have tried sticking to my usual size --- generally too tight. I have gone up 1/2 size - usually too big.

But I am still looking.

I have problem feet too. I wear clogs almost everyday or Go Walk with the faux fur lining in the wintertime.

I have found that SAS makes good shoes for "bad" feet. They all have a footbed that is removable so an orthotic can be inserted. They are not high fashion shoes, but some styles can be dressed up so you look decent whe wearing a dress or skirt. They come in a ton of colors and special sizes. I have listed 2 styles as an example.

They can be purchased on line, but I have an outlet store near me.

On 10/29/2014 happy housewife said:

I have dressy flat shoes. They are out there. Go to a good, high end shoe store and tell them what you need.

I agree ... there are shoes out there.

Thanks, ladies! You're so sweet! I am trying on and trying on!! I am hoping I do find at least a pair or 2. I have had good luck with Clark's in the past, but so far am not having any luck with regards to this need. You take things for granted and then all of a sudden --- you can't wear any shoes and can hardly walk! Take care, all!