The Fascinating Mystery of Anna Wintour’s ‘Go-to’ Lunch

Hold the tomatoes, please. Photo: Gilbert Carrasquillo/GC Images

Anna, the new Anna Wintour biography, is 430 pages long. Author Amy Odell spent four years working on it, interviewing more than 250 sources. It is the most definitive text on the Vogue editor-in-chief’s life to date, and it’s filled with fascinating details, like the time Wintour’s colleagues allegedly saw her throwing out pennies while she was working as an editor here at New York. But it was another sentence of Odell’s that stopped me cold when I first read it, and it’s haunted me ever since: “In fact, Wintour’s go-to lunch, after Condé Nast moved offices to 1 World Trade Center, was a steak and caprese salad without the tomatoes from the nearby Palm restaurant.”

You could argue that Wintour became the most powerful magazine editor in the world specifically because of her taste. She is famously meticulous about every single detail of her life, even going so far as to ban chives from the Met Gala’s menu because they might make guests’ breath smell bad. It does not seem like an accident that she would ask to have the tomatoes removed from her caprese salad. Odell’s book places this order as something Wintour would have eaten five or six years ago — but still, it remains deeply confusing.

What even is a caprese salad without tomatoes? The entire dish consists of only three ingredients: tomatoes, mozzarella, and basil. (Delicious together, and also a nod to the colors of the Italian flag.) To lose the tomatoes is like ordering fish and chips without the fish, or macaroni and cheese, hold the macaroni. As an Italian, I’m offended. As a journalist, I’m captivated.

I understand that, as an editor, it is Wintour’s job to make cuts, to highlight the best qualities of any given thing, and to trim away the distractions. But I worry her subjective preferences in this case have gotten in the way of Objective Truth: that tomatoes always belong in this salad. In Anna, the sentence preceding the shocking caprese line offers some possible insight into Wintour’s thinking: Miranda Brooks, Wintour’s landscape designer for her house in Mastic, Long Island, told Odell that she tried to convince Wintour to plant a vegetable garden on her property, but she wouldn’t because “she doesn’t like vegetables.”

Of course, tomatoes are a fruit, but it’s possible Wintour’s aversion extends to eating food that might be considered vegetable-adjacent. (She likes potatoes, reportedly.) People should eat whatever they want, but I still had questions. Isn’t this order just going to be cheese? And if so, why not ask for that? Wintour declined multiple requests to be interviewed for the biography. Sources at Condé wouldn’t offer much insight, and neither would reps from the Palm. So I emailed Odell — who notes in the back of her book that two different people told her about this lunch order — and she got back to me right away with more information.

“The lunch would have been picked up typically by the second assistant,” Odell explained, adding that Wintour’s order would arrive with a proper plate from the restaurant so that she didn’t have to eat off of paper or plastic. “You know how in The Devil Wears Prada we see the assistants throwing the plate in an office sink?” Odell elaborated. “In more recent years, the plate was packed up and sent back to the Palm, which then cleaned it.”

Equipped with a full understanding of the situation, I knew what needed to happen next: I would have to order this lunch for myself.

Conveniently, New York’s office is next to 1 World Trade Center and also located within walking distance of the Palm in question, so on a recent weekday afternoon, I called them. “I’d like to order a steak to go,” I said. When the host asked me what kind, I realized this detail had been neglected, so I went with a medium-rare filet mignon because, well, I figured it sounded like the fanciest option. (Also, I don’t think Wintour is eating a rib eye for lunch.)

“Anything else?” the host asked. I took a deep breath. “Yes,” I replied. “I’d like to order a caprese salad, but hold the tomatoes.”

There was a beefsteak-size pause on the other end of the line. “So,” the host began, “you just want the mozzarella … with the lettuce leaves …?” He sounded confused and mildly distressed.

“Yes,” I replied. “Mozzarella and basil, but no tomatoes.”

“Okay then,” he said.

Okay then. My order would be ready in 20 minutes. After tax and tip, lunch cost me $77.33.

The final order. Photo: Emilia Petrarca

At this point, PTSD from my days of being a fashion assistant kicked in and I suddenly became very nervous. I did not want to mess this up. My instinct was to leave immediately, even though the restaurant was only about five minutes away. But my real concern was making sure I got back to the office before my food turned cold. As soon as I picked up my brown paper bag with “!! NO TOMATO !!” printed on the receipt, I booked it back across the street, even running a red light in the name of medium-rare. If I were headed to Condé Nast, I would have been there in three minutes and 15 seconds flat. (I timed it.)

When I got back to my desk, I ripped open the bag to find two small plastic containers that were “sealed for my safety.” I don’t know what I was expecting — certainly not a ceramic Palm plate — but at best, my haul looked like an organ donation, and at worst, airplane food. This is why Wintour’s assistants went to such great lengths to make it look appetizing, I assumed, and no doubt why the restaurant would agree to send and retrieve a plate, as well. Presentation is everything.

Because I don’t have an assistant (or a second assistant), I was forced to make do for myself. I got a recycled paper plate and some plastic silverware from our office kitchen and found an empty conference room where I could sit, partly to spare my colleagues from any wafting meat aromas, and also because I wanted to pretend that, like Wintour herself, I had a huge office with a view.

I then plated the food as neatly as I could, drizzling the provided olive-oil dressing over the mozzarella like it was a blank canvas. Compositionally, though, something was still missing: the color red.

The complete lunch. Photo: Emilia Petrarca

I cut into my filet and winced. It was not medium-rare, as requested, but instead rare. Had I gotten back to the office too quickly? If I were my own assistant, would I fire myself for such a grave oversight? How dare I serve this undercooked meat to myself. I decided to go ahead and eat it anyway.

Chewing a bloody hunk of meat alone in a conference room, I felt powerful and vaguely medieval. For a split second, I thought, Maybe I understand Anna Wintour. But then I remembered the tomato-less caprese on my plate and quickly snapped out of it. The two slices of cheese the Palm gave me were thick and pillowy, as mozzarella should be, and the basil was visibly fresh. I enjoyed a few oil-and-juice-soaked bites and could maybe — maybe — understand why someone would order it this way instead of just asking for some plain mozzarella, since the dressing did add a little bit of excitement. But it wasn’t long before I missed the brightness that tomatoes would have added. Without them, the experience felt a little like stuffing cotton balls in my mouth. I was overwhelmed. There was more cheese on my plate than steak, and I just couldn’t finish it. Even if it had been on a Palm-branded dish, this particular desk “salad” would still feel sad.

Thankfully, Vox Media, New York’s parent company, is a pro-vegetable organization and provides cute little baggies of baby carrots in the office fridge, which I immediately grabbed to supplement my luxury lunch. They weren’t red, but they would have to do.

The Fascinating Mystery of Anna Wintour’s ‘Go-to’ Lunch