If you go to Milan and do not have the money for the fantastic Italian suits you see there, take a look at Boggi. Boggi is in Milan (of course) and they have a fantastic staff. Not only do they offer great tailoring, style advice, and service but they also do it without breaking the bank.
Their online store really does no justice to the selection and quality of their product, but check it out here.
If you do go to Milan, ask for Davide, he’s the one who knows what the young gentleman wants.