We will be visiting Rome, Tuscany, Florence and Venice in March 2018. Looks like fairly cool weather (upper 50s-low 60s) and maybe some light-moderate rain. Interested in suggestions for daily walking shoes and then what people wore for dinner in evenings. We are moderately active women in our 50s who respect a "sensible shoe" but still like a little style.
I don't even bother bringing anything with a heel, unless it's a wedge. The streets are just too uneven, and I value my ankles and knees over style. I only took 2 pairs of shoes, which I alternated every day or so. One was a pair of black leather Keds which I wear with a set of slip in orthotics. The other was a pair of black Clarks slip ons, also leather, with a slight wedge heel. Both were sprayed with waterproofing and withstood a downpour in Venice. Since I only wear pants, these were sufficient for dinners out in the evening. But we weren't dining in Michelin restaurants or going to the Opera.
But everyone's foot is different. I went to a good shoe store where they measured my feet properly, and just kept trying on shoes until I found ones with just the right amount of cushioning and arch support.
Years ago a friend recommended a waterproof goretex shoe for Rome in February. The weather was mixed. When it rained, water gushed down the sidewalks. I was sure-footed and my feet remained dry and warm. My current pair are Salomon. On many trips to Europe, that is the type of shoe I wear for touring. Depending on the season, I take a pair of sandals or black flats to wear in the evening.
I used Echo's for many years and was happy. I tried a pair of Skechers GoWalk 4's when we were in Belgium last year and absolutely loved them! We walked throughout Bruges, Ghent and Brussels for many hours every day and I did not feel tired or soar. They are definitely worth trying and very reasonably priced.
We just got back from Florence and I would also add some more tips on the soles. We found in the spots we stopped in Italy (Milan, Aviano and Florence to be brief), the stone walkways were a bit rough which mean the shoes gripped wonderfully. My wife had a very comfortable pair of boots, but, they didn't work well in Florence as something that is very comfortable walking on smooth streets and malls of Dallas were painful after a which walking on the uneven streets and walkways of Florence. I took a worn out pair of dress shoes that I planned to discard there in Florence and purchase a pair of real Italian shoes. OMG... we looked a bit but I found some great walking shoes that worked great and they were waterproof too.
Comfort is by far and away the most major determining factor. If your travels are anything similar ours, you will put miles on your feet and shoes.
As you can imagine, blisters or aching feet would certainly put a real damper on an otherwise great trip. I would suggest selecting a pair of shoes that you already have and know are comfortable. It's not the time to break in a new pair of shoes.
But I carried to Italy had a dressy upper but the soles were as rugged as good walking shoes. They were sufficient for hours and hours of walking and I even did some light hiking in them. Also took some sandals for evening.
Happy feet make all the difference. Unless you are going to upscale restaurants for dinner, don't bother. Women in their fifties in Italy who like a little style will probably be wearing Italian leather boots, days and evenings. You might consider buying a pair . . . but be sure to take some moleskin and blister bandaids in your evening bag.
I'll be there around the same time and will be wearing bringing low cut boots, Paul Green short lace-up euro-style black walking shoes, and a pair of leather flats with good arch support for dinners.