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Jean Structure

While the company has several styles, it's their High Roller stretch-fabric jeans that separate Jack of Spades from the rest of the field. The pants are infused with two percent elastathan and 22 percent nylon, which offer flexibility without sacrificing fashion. Ken Giddon, president of Rothman's clothing in New York, praises this unique material. "These guys are experts; they've figured out how to make a product that is complimentary to a large part of the population," said Giddon. "It is our best-selling pair of jeans."

His jeans ($145) are the The High Roller by Jack of Spades. His shirt ($95) is by Lenor Romano. His jacket ($164) is by Geox.

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