First of all, a note on methodology: I am breaking the rest of the Vanity Fair red carpet looks into two categories. This one, as implied by the headline, are the looks that really went for it and tried SOMETHING, successful or otherwise. The post coming up after this will be the “safer” options from what remains of the red carpet. PLEASE NOTE THIS IS SUBJECTIVE! I AM NOT A FASHION SCIENTIST! Some of these are risky for the person in question. Some of them are only lightly bold.

That out of the way…some of them are heavily bold.

[Photos: Matt Baron/Shutterstock, Broadimage/Shutterstock, David Fisher/Shutterstock, Casey Flanigan/imageSPACE/Shutterstock]