In short, no you don’t have to be a fashionista when you travel to Italy. Italian women have been cultivating their style their whole lives. I do encourage you to embrace some of their strategies—solid and less colorful interchangeable separates that can be mixed and matched, use accessories to add color, texture and “pop” and change up your look, fewer nicer quality pieces, and less is more.When I travel, my goal is to not look like a tourist. It helps in several ways. Firstly, I am less likely to be a target for pickpockets (I have never had a problem with pickpockets and the Italian police crackdown on anyone targeting tourists since tourism is an important industry in Florence). Secondly, I can blend in more and get more of a feel for what life is like for locals. That being said you should dress in layers and be comfortable (wear shoes that will support you on the uneven cobblestone streets). Slacks or skirts are fine. It won’t be warm enough for shorts so no worries about whether that is even appropriate. Jeans that are nice, very new looking or black, are ok, but I am on the fence about whether that makes one stand out as a tourist more. You must have your shoulders covered in churches so toss a scarf in your bag that can double as a shawl. More on packing in our Florence guide that you will receive after you register.