Packing...my least favorite activity

So, I am packing my whole life into two giant sized suitcases for my move to Italy next week.  I absolutely hate packing, and this type of advanced packing sends chills of fear down my spine.  As I pack, I would like to get input from the readers about what pieces to pack, which to leave behind.

I will be working in a school with a "smart" dress code, so I will definitely need professional clothes.  Of course, though, I will be in Italy, so even my off-time clothes have to be chic.  I need things I can walk in, ride a bike in, and party in.  Obviously, I am going to need help...

This is my weekend project, so stay tuned as I post my dilemmas on the site.