Thirty years later, the comedy classic’s chill menswear feels more relevant than ever. “I was kind of dressing him as if I wanted him to be cute to college girls,” director Tamra Davis tells GQ.

Adam Sandler’s casual Oscars outfit was a highlight of the award show for many viewers. Sandler went against the Oscars' famously formal attire by wearing a blue hoodie and shorts to the award show.

Adam Sandler’s fashion sense, or lack of it, gained even more notoriety at the Oscars on Sunday as host Conan O’Brien mocked his casual look in one of the night’s skits. O’Brien ...