This is a big one. You have a handle on the language. You know how to order food, have small talk, ask for directions, and you want to blend in. So, what should you wear?
In American we judge a person the moment we see them–subconsciously or not. In Italy it’s much worse. You may not be going to Milan Fashion Week, but you want to be conscious about how you look. Fashion is important in Italy. This becomes obvious the moment you board the plane and you realize everyone around you is well dressed. And those that aren’t? They’re the Americans!
Why do people always say that Italian men are the most attractive in Europe? It’s not in the face, I can promise you that! It’s in the way they dress. Their skinny jeans are tighter than yours. Their hair is meticulously set (kind of like Nazis?). Not one eyebrow hair is out of place. With all of the effort they put into their look, do you really want to be walking around in a tank top and flip flops?
Don’t forget, the more you blend in, the less likely you’ll be a target to street vendors, pick pockets, aggressive outdoor restaurant hosts, and doting Italian men.
Even after all the effort, don’t fool yourself. After months in Italy, tirelessly practicing to erase my accent and dressing to blend in, I’ve only been mistaken for an Italian once. It was a glorious (and brief) moment and I’ll never forget it.