I don't know if he's supposed to be emulating his character from Leatherheads, or if he just felt like wearing a hat? Either way, he manages to pull off this old-fashioned look by mixing the driver cap with a more updated, sporty-looking jacket. This ensemble is classic and well put-together -- it's nice to see Clooney in something other than the usual sport coat and no tie. Part of what makes this outfit work is that he kept it monochromatic, but then again, he almost always does.