Leonardo DiCaprio has a history of picking out some well-dressed roles. From men like Howard Hughes in The Aviator to his turn as "Jay Gatsby" in The Great Gatsby, he's played some parts that require some serious dressing up. Being the avid cinephiles that we are, we sifted through his oeuvre (including obscure flicks like Don's Plum and The Foot Shooting Party, you film snobs) to find the parts with the freshest kits. And then we ranked them, because we're crazy. So sit back (consider pouring a stiff drink to get in the mood) and take a look through Leonardo DiCaprio's Most Stylish Roles.