What an appropriate question. I've been in Italy for the past three weeks (Florence and Milan) and was about to write a post on Italian fashion, but since you asked first... Italian casual is much more formal than anywhere I've seen. Men are wearing tight bootcut or pegleg jeans, either in dark blue or a semi-distressed fashion; no heavily battered Diesels. Levi's (507 and 501) and Replay are favorites. As for shoes, pointy toed black or vintage brown boots are prevalent. A quality pair can be purchased for around 120 euro. The most popular fashion right now is highly stylized shirts. I've seen shirts with as many as four buttons on the collar, double collars, and contrasting stitching on buttons and seems. Patterns are bold diagonal checks and strips, usually in bright reds and light blue. The only word to describe the collars is BIG. Expect to pay no more than 80 euro, and at the least 35 euro for shirts. The main thing that sets apart Italian men is the coats. I've yet to see more than a handfull of locals in leather coats. Everyone is wearing wool overcoats, 3/4 length, in every color except for black. Olive, brown, navy, and camel are the colors of choice. A great coat can be had for 150-250 euro. Any more questions, just ask..