Personally, and I don't think I'm going out on some undiscovered or any limb on this one, Band of Outsiders is one of the best men's and women's labels out there. Get yourself a Band of Outsider oxford, and you have the only shirt you need. Good to go.  And they take these Polaroid shots on their blog with celebrities and randoms to encapsulate an entire season, and it is just a brilliant look, really fits the mood of the brand. And Marisa Tomei is a good Italian girl. You can spend a lot of time to scanning all the shots... its like Mad Men 2010. 

I wish I was here.... right now....