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Dress Well at Any Age: The Right Way to Break Fashion Rules

Think you're too old to wear a miniskirt? Too young to pull off gray hair? Think again.
Andrea Fishkin - gray hair
Photo: Sergio Kurhajec
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O, Yes You Can!
Gray Hair at 31
Andrea Fishkin, a sales superviser and stylist, spotted her first silver strand right before her Bat Mitzvah; by 18 she was entirely gray. "I fought back by dyeing it," she says. "I suffered all through my teens—I was so insecure about the slightest bit of roots showing." But seven years ago, Fishkin decided she was sick of all the upkeep. "I'm so much more comfortable with myself now, and I think that comes across," she says. "I used to wear all black, but that isn't me anymore." This teal gown plays up the contrast between Fishkin's striking gray waves and her calendar age, thanks to its sexy silhouette and vibrant color.

To complement gray hair:
Don't compete with it. When your hair makes an extreme statement, keep jewelry to a minimum. Glowing skin is your best accessory.

Add youthful touches. Fishkin's dress has a high slit, a plunging neckline, skinny straps, and a body-hugging shape.

Gown, Edition by Georges Chakra
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From the May 2011 issue of O, The Oprah Magazine
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