Anne stopped by the David Letterman show in an ensemble that will inspire those hesitant to dabble with the moody combination of navy and black. Her pajama-style Marc Jacobs wrap dress from the Resort line looks super sophisticated against black accessories like opaque tights, patent Brian Atwood pumps, and a black Ferragamo woven bag. The oval turquoise earrings and chunky gray cocktail ring are nice, simple touches. So, does Anne have you convinced?

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