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.
See more from Vanity Fair:
Two Decades of Brad Pitt
International Best-Dressed List
Classic Nude Portraits: Lady Gaga, Angeline Jolie, Jennifer Aniston