What Do You Wear When Breaking the Ultimate Glass Ceiling?

When Hillary Clinton joined Twitter, she typed out the facts of her famous résumé, then added, “dog owner, hair icon, pantsuit aficionado.” Exactly one year later, she published her memoir, Hard Choices. In it, she joked that she might have called the book “The Scrunchie Chronicles: 112 Countries and It’s Still All About My Hair” instead. Making a punch line of extensive ’do coverage is one way Clinton has found to push back against scrutiny, not to mention sexism. In a commencement speech she gave in 2001, Clinton, then a New York senator, told graduates from Yale, neatly seated in rows, “The most important thing I have to say to you today is that hair matters. Pay attention to your hair, because everyone else will.”

Among other challenges Hillary Clinton is facing is: How can a woman look presidential? When it comes to image, there is no template for the way the most powerful person in the country ought to dress if that person is female. Hillary Clinton is the closest we’ve come, and there’s forever been a tizzy about her appearance, a constant undercurrent of controversy and second-guessing. She wears a V-neck, and that’s showing too much skin. (In 2007, the Washington Post devoted a whole article to a peek of cleavage: "It was startling to see that small acknowledgment of sexuality and femininity peeking out of the conservative—aesthetically speaking—environment of Congress. After all, it wasn't until the early '90s that women were even allowed to wear pants on the Senate floor.") She covers up, and the late designer Oscar de la Renta calls her “sort of very prudish.” For years, Clinton has been inclined to favor the nondescript, even bland: That’s seemed safest.