Earlier this year, Anna Wintour visited Obama headquarters in Chicago to talk numbers with the campaign’s top fund-raising brass. As she headed into her meeting, Wintour passed a tray stacked with food for volunteers: glazed doughnuts festooned with bacon, classic campaign fare. “I trust you’re not interested in that,” a staffer jokingly offered. She fixed him with her cool, disdaining stare. There will always be certain, crucial differences between politics and high fashion—“wedge” shoes or issues?