When America met Michelle Obama —for most of us, at the start of her husband's campaign for president—clothing was all about efficiency. On the campaign trail, she opted for Maria Pinto sheath dresses in bright colors like tangerine and teal. “It was practical for campaigning because, while we were there doing that rally that night, I was probably at a farm festival and then at a school,” she says. “It’s never just one event.” Turning to her glam team, she adds, “Could’ve used y’all back then!”

Cut to election night, 2008. Obama didn’t give much thought to her look until a week or so before. She purchased a black and red dress from Narciso Rodriguez’s spring 2009 collection. “I wanted it to feel vibrant, I wanted it to feel alive—but I didn’t have a whole lot of time to think about what

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