What if Anna Wintour Ditched Her Bob?

Photo: Michael Baumgarten/Trunk Archive

Until about six months ago, I had something in common with Kim Kardashian, Vogue editor-in-chief Anna Wintour, Ellen Degeneres, and Gwyneth Paltrow: a signature hairstyle. For about four years, I sported a short, blonde pixie cut; it was my look. Last spring I made the decision to grow it out, and I’ve been suffering from a bit of an identity crisis ever since.

It all started last year when I met Rossano Ferretti, the man who cuts Kate Middleton’s hair. (Another lady with a signature ‘do!) He told me I should “go softer.” I’m not usually that swayed by other people’s opinions, but when the man who takes care of what is arguably the softest hair in the entire world gives you advice, you listen. And honestly, I was kind of sick of the lack of styling options with short hair. So I embarked on a grow-out adventure.

To start, growing out short hair takes a lot of mental endurance. I had recurring thoughts like: “Why the hell is this taking so long?” and “Oh my god, how long will my hair look like Jim Carrey’s in Dumb and Dumber?” (Answer: three months.) Along the way I got frequent trims so it would still look like I had a style, which just slowed the process. I wore a lot of baseball caps.

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Then people started saying things. After not seeing some colleagues for most of the summer, I showed up to a work event and several people said of my new almost chin-length hair, “Oh, but you looked so good with short hair!” (So now I look bad?) And the worst, “Oh, I didn’t recognize you!”  The truth is, I don’t much recognize myself lately either, and it is stressing me out.

According to Dr. Alice Boyes, a psychologist who has a book about anxiety coming out next spring, my feelings are understandable. “It’s quite confrontational when other people react to your appearance because there’s an internal process you go through when you’re thinking about changing something,” she said. “It’s like when you lose weight. When other people comment, it can feel like a real intrusion. You’ve really got no control over what people say or how they react.”

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The other part is that when you grow out your hair, you don’t have a consistent look from week to week. It constantly changes, sort of like being pregnant. One minute you can fit into regular jeans, and the next minute you need elastic-waist pants. Every morning in front of the mirror is an adventure with bobby pins and headbands. For a person who’s a creature of habit, like me, never knowing exactly what I’m going to see when I look in the mirror just adds to my feeling of unease in my own skin.

My hair was a big part of my whole look. I like to wear black and interesting earrings and studs and leather jackets—the extreme hair seemed to just go with this outward persona I’d crafted. “Choosing how you style your hair or the color of your hair is such a statement that people make,” Dr. Boyes says. “Especially for short hair, because it’s quite a bold thing to do. Other people often see it as a statement of toughness, or going against the grain. You have to be very disciplined to keep it short all the time.” I felt like I was giving up the edgy, risk-taking part of my personality. (Which is insane since I take the NYC subway and that’s obviously the biggest risk I take everyday). But I looked like someone who might possibly do something unexpected.

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Obviously I can just chop it all off again if this identity crisis persists. People who cut their hair short and then have regrets can’t fix things quite so easily. But that would feel like quitting and also admitting that I am incapable of change. So I wait and grow at a snail’s pace. The other day I was able to put my hair in a tiny, scraggly ponytail, and it was a glimpse of the new, more versatile, me.