Barack Obama getting in touch with his inner Dukakis
As the above picture illustrates, even the coolest of Democrats have more than a little Michael Dukakis in them. In conservative circles, we often lament how Democrats have forgotten the foreign policy legacy of John F. Kennedy. Well, they've also forgotten JFK's campaign legacy. JFK knew a thing or two about appearing cool. And he virtually never wore a hat in public after sporting the traditional (and ridiculous looking) silk topper for parts of his Inaugural festivities. Legend has it that Kennedy even formulated a maxim declaring that politicians should never wear hats in public because a hat can make you look silly. For evidence of the maxim's probity, please see the above image.