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Michelle Obama

Michelle Obama's look is reminiscent of Jackie O.'s imitable style, making her outfit an instant classic.

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Michelle Obama

Getty Images/AFP – Emmanuel Dunand

With a fashion sense that is frequently compared to that of Jackie Kennedy Onassis, Michelle Obama pairs unfussy dresses with faux pearls to achieve a look that is simultaneously classic and modern. "She always look confident, comfortable and polished," says Deana Bracken of GreenWithGlamour.com. "She has a real handle on her own style and accessories."

Amazingly, Obama does not have a stylist (or so goes the party line trotted out by her spokesperson), but she is known to frequently work with Chicago's Maria Pinto, the designer of the vibrant purple sheath Obama wore at the Democratic National Convention. Paired with her favorite pearls and an Azzedine Alaia belt, the Pinto ensemble won accolades in the press.

"The Alaia [belt] shows she's a little bit of a fashion insider, but it's more of her intelligence and independence that shows through," Amy Fine Collins, a guardian of Vanity Fair's International Best Dressed List (which included Michelle Obama in 2008), told the Associated Press.

Simply Vibrant Dress

An attention-grabbing purple hue and figure-flattering rushed waistline turns this simple silhouette into the perfect day-to-evening dress. Take a cue from Obama's playbook and play up the classic V-neckline with a strand of chunky fake pearls.

All-Purpose Black Belt

Hand-embossed diamond detailing gives this belt a luxe look that would look as great with a pair of jeans as it would cinching a black blazer. Pair it with the Ojai dress, turning the buckle to the back, to achieve Obama's sleek look.

The Perfect Pumps

Finding the perfect pair of black heels is like stumbling upon the Shangri-la of fashion. The pointy toe and mid-heel height give these a hearty dose of class, but the modern buckle detail proves these aren't your grandmother's pumps.