When I was in Milan, I got a gig during fashion week to do street style photography both in Milan and Paris for two season. It was a blast. Probably one of the funnest things I’ve done.
The first day, I sat by the Duomo all day and snapped photos of people that I thought were stylish, weather they were there for fashion week or if they were just there visiting and shopping. It’s kinda funny that some of the people that you run into, you will eventually see and meet at the shows while photographing street style. This was kind of done as a mistake. I didn’t know how fashion week worked and I was in Milan! I imagined that you would run into a model every 15 paces where ever you go. That’s not true. There is an orderly schedule for all of the shows at multiple venues all over Milan. One of these guys I’m pretty sure was homeless.
This is a really good exercise to break your shyness as a foreigner. Go out with a camera and stop cool looking people from every other country than the one that you are from, and that speak every other language you don’t know, and ask them if you can take a picture of them because you like their style. Then ask them for their name and what they are wearing. It really helps your communication skills.