Mickey Drexler knows who to turn to with a style question, and now the rest of the world will, too. Jack O’Connor, the in-house men’s stylist for J. Crew, recalls the day Drexler, the company’s chief executive officer, called on him in front of a roomful of people during a design presentation. “He put me on the spot in front of around 50 people by asking what shirt and tie he should wear with a suit. I came up with the answer immediately and he thought that was great, and said: ‘Jack knows best.’”

That line became fodder for the company’s employees, who started turning to O’Connor for fashion advice. Now O’Connor features in a new media campaign, “Jack Knows Best.” J. Crew turned to Saimon Chow to create a short film that is streaming in 6,700 taxicabs in New York City during fashion week as well as on YouTube. The minute-long film will be on the J. Crew Web site starting next week and there will be an Ask Jack section there, as well, featuring four frequently asked questions, such as what a man should wear to a wedding and when to choose a two-button jacket over a three-button.

This story first appeared in the September 18, 2009 issue of WWD.  Subscribe Today.

The video stars “The Unsure Man,” who changes his clothes dozens of times as he ponders the appropriateness of his outfits. At the end, he holds up a sign that reads: “Help,” and in swoops O’Connor, “Style Confidant,” to tweak his wardrobe. The video ends with the line: “For style advice, tips and questions, jack@jcrew.com.”

O’Connor said the questions since the spots began airing have ranged from how to tie a tie for special occasions to whether black shoes can be worn in the country and brown in the city. So is he feeling overwhelmed by his new role? “A BlackBerry really helps,” he said.

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