What to wear in the evenings

If it's the same as in Paris, matching a beautiful top (which you could wear any time in a city) with nice black slacks will work fine. When you are sitting at a table, the top is what shows. What I am wondering about is shoes when I dress up- European women wear very stylish boots or shoes- not practical when traveling. Any suggestions, anyone?

I'm glad you asked that question; I am going to the same places and wondering the same thing...

Would it be frowned upon to wear a pair of flip flops? I can't even believe I just asked that based on the previous post about fancy boots/shoes...

Can one get away with wearing leather walking shoes?

I have learned from Rick and from taking too much luggage on the first trip to Italy. I go with pants and wear a pair of leather Munro shoes.You can dress those black pants up or down. We travel with 21" carryon and he carries a backpack & I carry a daypack. I pack black & tan pants. Every shirt, 1 vest & 1 jacket go with either color pants. Granted, when you look at the pictures of our trip, it looks like we've been gone for 5 days instead of 3 weeks.
Works for me! Buy a pretty scarf or 2 to dress up your tops, especially Florence and Venice.

As far as the Italian women wearing very stylish shoes, yes they do, but they are not traveling out of a suitcase. And they are used to walking over those cobblestones in heels. I don't see how, but they do. I wouldn't wear flip flops to a restaurant at night, but I don't think they would turn you away if you did. For me, I want to look decent, but I want my feet to be comfortable also.

I hope you all have a great trip! We leave Thursday for Rome & to meet a RS trip!

On my 2 week RS tour, I took one of those black broomstick type skirts...rolled well in suitcase, and I wore it several times for evening meals. On my 2nd trip, took only a few pair of black pants, and did fine. Either way is easy and presentable. I wore black Ecco sandals in the evening as a comfy change from all day walking shoes. I agree with others, a few colorful scarves...buy them over there as a pretty, useful and fun souvenir, and a few pieces of inexpensive jewelry. For me, the trick is stick to black with another color or two for tops, and you're good to go. Ciao and have a wonderful trip!

Are short pants or long pants both acceptable?

I'm guessing that the long pants would be more versatile though since they'd be easier to "dress up"?

I heard it's pretty warm/humid right now, and I do tend to get a bit uncomfortable in extreme heat. Maybe I'll bring one long pant and one short pant?

The last two trips I took to Italy I packed a jersey knit skirt or a linen skirt. Both were black. I took one nice t-shirt that was a bit more "dressy" than my cotton t's for day time touring.

Of course, each evening I had on the same outfit I wore the night before, but we were in different places, so only my husband knew I was wearing the same thing again and again.

I wore my black webbing sandals (Chaco brand, about 6 years old, but my go to shoes for travel)

I took a pashmina with me, or purchased a scarf as a wrap.

The skirt will take up minimal space in your suitcase, and comes in handy during hot days of travel in place of pants.

In any case, your pants would be fine too. I just like one skirt on my trips for warmer days, or nicer dinners!

Most of these suggestions look good. I did just read a Rick Steves article posted on CNN website where even he thinks that shorts and a t-shirt for dinner in the evenings in Italy is "goofy".