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The street style star: Recall all those great costumes ruined by the necessity of a Winter coat on a cold October night? That's never been the case for the creative director of J.Crew, who is the ultimate professional in layering.
The costume: Make like Joey from Friends, and put on everything in your closet, including a pair of black-frame glasses. But whatever you do, do not put your arms in those coat sleeves. That's as scary a thought as playing Bloody Mary with your friends in the bathroom.