Dress shoes in winter?

Kathleen, if you can wear warm socks with your walking shoes, I'd go for a somewhat dressier flat with the comfort sole as second pair, especially if you plan evenings out. They must feel really good, though, and be well broken in. Or you might leave room in your bag for a pair of Italian shoes....

I'd go for the second pair of walking shoes. We are talking so serious cobblestones....Have a great trip!

May I suggest a nice pair of knee high leather boots? They are warm in the winter and they never seem to go out of fashion here. And you can wear them with jeans or with skirts and dresses, good for day or evenings.

Thanks for the suggestions. Does anyone have specific brands and/or styles they would recommend? I know lots of people on here like Eccos, but I seem to be in between sizes on the ones I've tried.

And Claire- do you wear boots with a heel or without?

I wear both. I have a pair which has a heel AND manages to be comfortable, but as long as it isn't a stiletto heel the cobblestones won't be a problem. Seeing as you are bringing walking shoes for the day, why not bring boots with a (lower) heel for evenings? Women of all ages wear boots here and in January that's about what everyone is wearing, especially for evenings out.

To test out your proposed shoes, wait until the ground has frozen in Minnesota. Go out to a plowed field and see if you can walk in your shoes. That should prepare you for the cobblestones of Italy.

With the way our weather has been recently, it might not be long until the ground is frozen solid. My plants had frost already this week.

We do have some streets near downtown that are brick, so maybe I should test out my shoes there. Boots might be good as that's something I would get lots of wear out of at home too.

Dansko Meredith is wonderful. That particular style is discontinued now, I think, but Dansko has similar styles. That shoe is in the Golden Gate line, which I find, for me, is particularly good for walking during traveling - has a thick but stable "rocking" sole. So comfortable for miles of city walking.

I agree with the boots suggestion. I live in Italy and also live in my boots from November to March. For evenings, I wear them with tights, a skirt and nice top. Mine are flat, more comfortable and easier to walk in.