Director: Rob Reiner
Release Year: 1987
Costume Designer: Phyllis Dalton
Who vs. Who: Westley (Carey Elwes) vs. Inigo Montoya (Mandy Patinkin)

Unless you're The Rza in Bobby Digital mode, the eye-mask accessory and cape combo is ill-advised. There's a time and a place for everything, and the Renaissance-era fairy tale land seen in The Princess Bride is that look's perfect setting. On Cary Elwes, the Zorro-like design is dashing as hell. And, we'll admit it, the same goes for Mandy Patinkin's brown leather pants. Is it Halloween yet?