looking elegant - being comfortable in Italy

Hi Michele, I'll be traveling back to Italy in September and would like to dress a little differently this time. Italian women are so elegant! What types of clothing basics would you recommend for traveling in rural areas as well as to the cities of Florence and Rome. On my past few trips I've worn flat, extremely comfortable sandals by Simple, but feel they are a bit unsofisticated, although I do need something that I can walk in, especially on the cobblestone streets and marble floors. Clothing-wise I'm not sure about. I've consulted with Simplement Chic for colors and clothing so have a good idea about styles that work best for me. What do you think about jeans for daytime? I know they are popular in Europe, but probably with a heel or boot. I look forward to hearing from you.