Ah, sanity. It can be so aesthetically limiting. Thankfully, not everyone feels bound by its strictures. Ever the trend-setting bunch, some of Hollywood's brightest stars--and many more of its dimming ones--have boldly sacrificed the purported virtue in the name of head-turning style. This season, we're ripping a page out of their medical records and showcasing these definitively #winning looks. Reese Witherspoon, we hope you're taking notes.