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The Navy Blazer: Work
For maximum flattery, look for a slightly shaped, unboxy jacket.

As authoritative and fail-safe as a matched suit, but fresher: A navy jacket (Esprit, $160)—in a seasonless cotton blend—and gray flannel pants (Express, $80) are great for a financial professional like Joy Booker, 38, who works at an investment-management firm. But a witty surprise—a top striped like a man's tie (Kate Spade New York, $225)—is not against corporate rules. 

Belt, The Jack Rabbit Collection. Ring, Kenneth Jay Lane. Shoes, Furla.
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