Calypso crinkled silk dress

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Splurge on a sexy, silk dress—the perfect outfit for a girls' night out or first date. Oprah says the best thing about this dress is that it fits no matter how much you've eaten, comes in colors you can dress up or down and the more wrinkled it gets, the better it looks.

Available for $185 at Featured in O, The Oprah Magazine, March 2006.