Wear this watch like the members of defending America's Cup champ Oracle Team USA do, and you can take advantage of its mechanical movement, regatta countdown, and rotating bezel. It also has 500 meters of water resistance (which we hope you'll use in a scuba scenario and not in a boat race). [$5,500; tagheuer.com]
Mad Men's Charming Rogue
The man who played Roger Sterling, is moving on – surfing in Montauk, hanging with his son, and directing a feature film.
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