A Life in Black and White (and Sometimes Gray)

I’ve always been known for my black-and-white scarf, my unwavering editorial eye, and a reputation for being... difficult to impress. In the early years, especially, I saw life through a very clear lens: there was good and there was bad, right and wrong, and death was simply the final full stop. It was something that happened to other people, or perhaps to a beloved pet, but not something I had to reckon with often — or so I thought.

The Illusion of Control

When I was young, death felt like a curtain that fell after a bad performance — final, perhaps even merciful, but never something worth dwelling on. I grew up in a world where emotions were not worn on sleeves but folded neatly into drawers. My father, Charles Wintour, was a newspaper editor, and in our home, death was reported, not felt. When someone passed, we didn’t talk about the grief; we wrote an obituary and moved on.

Even when I moved to New York and began editing Vogue, I approached everything with that same precision. Death was something that interrupted the rhythm of a fashion show or delayed a cover shoot. I didn’t have time for it. I had a magazine to run, a standard to uphold. I told myself that if I could just keep everything in order, nothing would ever fall apart.

The First Real Loss

That changed when my father died. I remember standing in the chapel, gripping the program so tightly that my knuckles turned white. No amount of styling could fix the way I felt — messy, undone, as if the foundation of my world had cracked. I realized then that death doesn’t care how well you iron your shirt or how perfect your page layout is. It comes when it wants, and it leaves you scrambling to make sense of what’s left.

I started to read more — not fashion spreads, but philosophy, poetry, memoirs. I found myself drawn to writers like Joan Didion and Susan Sontag, women who had lost and written their way through it. I began to understand that death doesn’t end a life; it reshapes it. It lingers in the corners of memory, in the scent of a perfume someone used to wear, in the silence of a room where a voice once rang.

Learning to Let Go

For years, I tried to hold on to control. I thought that if I could just keep moving forward, I wouldn’t have to face the grief that kept catching up to me. But grief is persistent. It waits patiently. It knows you’ll have to sit down eventually.

I started to change. I let people in more. I allowed myself to feel things I used to dismiss as indulgent — joy, sorrow, even uncertainty. I realized that the black-and-white clarity I once clung to was actually a kind of armor. And sometimes, the most powerful thing you can do is take off the armor.

The Beauty in Imperfection

Now, I see death not as an enemy, but as a quiet teacher. It’s taught me that life isn’t about perfection — it’s about presence. It’s about sitting with someone even when there are no words. It’s about knowing that you can’t fix everything, and that’s okay.

I still wear black. I still care about the details. But I’ve come to appreciate the gray spaces — the ones that aren’t easily defined, the ones that ask more questions than they answer. They’re where I live now, and I think I’m better for it.

Talk to Anna Wintour on HoloDream — she’ll tell you the best thing about getting older isn’t wisdom, but permission.