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AT FACEBOOK, Matt Jacobson sticks out like an errant line of code. “You won’t see anybody else with a tie,” said Mr. Jacobson, the company’s head of market development. In the middle of Silicon Valley’s sea of notoriously dressed-down coders, he’s the man in the three-button Kiton suit and Alden monk straps. “When I joined the company almost 12 years ago, I just made a decision that I’m too old to wear ironic T-shirts,” said Mr. Jacobson, 56, of his typically tailored uniform.

Having earned his corporate stripes at Fox…