I love seeing a guy that can do classics but still look cool and young doing it. I think the key with this guys look is that the khakis are not cut so big in the legs - his pants were actually more jean cut. Notice also his pants are sitting higher on his waist which is often a much more flattering way to wear pants.
So many American were their jeans really low and it just accentuates a belly.
So, I am finally catching up with my shooting here in Milan. For the rest of the trip I should be posting on a pretty regular schedule.