On the Oscars red carpet, it's all about cool drama for Nicole Richie. Her eyeliner is a throwback to '60s cat-eye cool, but she adds her own twist by adding complementary winged eye shadow. With eye makeup that daring, it's a good idea to keep the rest of the look simple — and that's just what she does. A ladylike updo and just a pinch of pink on her lips and cheeks balance out the look. Do you think this style risk works for her?

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