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It's 2009! Take a deep breath and blow off your old fashion rules. Pick a bold style; test a new shape; dabble in color. Here, six women who dared. 

"A new business requires a new image."


"I used to dress in head-to-toe Prada," says Melissa Skoog, 35, of her years as vice president of public relations for the iconic label. Sounds like every woman's fantasy—except that the designer uniform left no room for her own taste. Skoog's new project—as partner in an online style magazine (TheDailyEffect.com, launching next month) and co-founder of an e-commerce site (On1Ave.com, going live in June)—is allowing her to "find my fashion voice again. Since we're meeting investors, I need to look really put together." But don't think that Skoog has to wear nothing but high-end labels: This svelte herringbone sheath is amazingly well priced (Talbots, $158), while the cable-knit cardigan (Ralph Lauren Black Label, $655) is a softer stand-in for a jacket. Unmatched pieces aren't as foolproof as a suit, but the effect is fresher, more contemporary. The serious neutrals are balanced by the two shots of bright purple (sweater and shoes); a belt (J.Crew) adds shape and polish. 

Earrings, Irene Neuwirth; bracelet, House of Lavande Vintage; bag, Sang A. Shoes, Dior

Get the 5 keys to building a better work look

From the January 2009 issue of O, The Oprah Magazine
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