I Lived Like Anna Wintour

Get me Patrick!

Anna Wintour Diet Harling Ross Man Repeller-5

On a sunny Monday morning, I stand outside the building in which the Man Repeller office is housed and text two coworkers a question: “Can you please come down to the sidewalk and give me a piggyback ride up the stairs?”

Welcome to the Anna Wintour diet.

Like wine on the Whole30 diet or carbs on Atkins, walking up stairs with my own two legs is strictly verboten on the Anna Wintour lifestyle track. I base this stipulation on a juicy tidbit from Tim Gunn’s book Gunn’s Golden Rules in which he claims to have witnessed Anna being carried down five flights of stairs by her bodyguards because she refused to ride the elevator: “The bodyguards had made a fireman’s lock and were racing her from landing to landing. She was sitting on their crossed arms…I ran to the window to see if they would put her down on the sidewalk or carry her to the car like that. They carried her to the car. And I thought: I will never forget this.”

Neither will I, Tim.

Anna Wintour Diet Harling Man Repeller (5)

The piggyback ride is much appreciated because I am a lot more tired than usual, having been awake since 6 a.m. According to Anna Wintour’s daughter, Bee Shaffer, her mom rises at 5 a.m. every morning to play tennis. Since I am but a plebeian pretender — an un-bobbed novice, if you will — I allow myself an hour more of slumber. When my alarm goes off at 5:59 a.m., I peel myself out of bed, dig in the back of my closet to locate an old squash racket I haven’t touched since college and proceed to bounce a ball against my bedroom wall (quietly, so I won’t wake my still-sleeping roommates). After finishing my “tennis,” I head to a 7 a.m. Pilates class. Pilates is not specifically part of the Anna Wintour diet. I just need to kill time before work. (A good Anna is never idle.)

When I sit down at my desk post-Pilates and piggyback ride, I realize that I am not wearing diet-appropriate garb. I know this because a) no part of my outfit is made of tweed b) my sleeves are not capped and c) I forgot my sunglasses at home. I resolve to do better. That night, I go uptown to my parents’ apartment and raid my mom’s collection of exceedingly ladylike but slightly stuffy clothing from the ’80s. I emerge with two Wintouresque blazers and one skirt-suit.

Anna Wintour Diet Harling Man Repeller (6)

The next day, I arrive at the office ready to kick ass and take [insubordinate coworkers’] names. I consider a British accent but decide to spare people that particular social abuse. There’s nothing worse than a bad fake accent, and mine will likely resemble the linguistic tragedy that was Anne Hathaway’s in One Day (watch this clip and thank me later for the unintended laughs).

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I toss my coat next to one of our wonderful interns and ask her to get me “Starbucks. Hot Starbucks.” Then I feel a crushing wave of guilt and add, “Please! Also I’ll never ever ask you to do this again! And get one for yourself — on me!”

I turn on my computer and wait for the latest Apple update to install. “By all means, move at a glacial pace,” I whisper to the rainbow wheel of death that appears in lieu of my cursor. “You know how that thrills me.”

Lunchtime presents a uniquely exciting opportunity for Anna Wintour diet protocol. According to a gossipy Page Six article, Anna was overheard ordering a salad of arugula, chopped apples and sliced avocado with “no dressing” at the restaurant Bistro Chat Noir, despite the fact that none of those items are listed on the Bistro Chat Noir menu. I attempt my own version of this blatant disregard of social mores by asking for smoked turkey in my salad at Sweetgreen even though I know full well that Sweetgreen does not offer smoked turkey as a salad ingredient.

“I’m sorry, we don’t have smoked turkey here,” my poor salad mixer informs me.

“Okay, I’ll settle for raw,” I joke.

“We have…chicken?,” she says with a look of concern.

That’s the main problem with living like Anna Wintour when you are not, in fact, Anna Wintour: you can ask for a special salad, but that doesn’t mean you’re going to receive it.

Anna Wintour Diet Harling Man Repeller (8) flip

Apparently, one of Anna’s go-to meals is a hamburger with no bun. I personally have little-to-no interest in eating a piece of circular meat with zero gluten accompaniments, but no one ever said this lifestyle would be easy. I heat a veggie burger in the microwave; a viable rebellion for the beef-averse. I finish it in five bites, after which I am totally stuffed. Kidding! I am still starving and handily polish off an XL bag of popcorn plus approximately 17 Hershey Kisses. Anna just turned over in her grave [of ex-assistants].

First thing the next day, I head to Elizabeth’s desk for a “run-through” of the products she’s called in to shoot for Instagram editorials. I ask if I can call her Nigel. She rolls her eyes.

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Look at these Holly Dyment rings!!!!!! I want one for each finger.

The stuff is great, but I’m a little disappointed I didn’t get the chance to lecture anyone about the origins of cerulean.

To make up for it, I decide it’s high time I procure an advance copy of the eighth Harry Potter book for my imaginary children (ed note: an eighth Harry Potter book does not and never will exist — at least to my knowledge).

I text my friend Anne, who works in publishing:

anna wintour diet harling man repeller

Is there anything more unethical than leading a friend or any fellow human to believe that an eighth Harry Potter book is impending, even if only for a second?? This diet is getting to me. I wipe away a guilt-salted tear. Good thing I’m wearing sunglasses.

Photo by Krista Anna Lewis; iPhone photos by Harling Ross. Featuring Versace sunglasses.

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  • Andrea Raymer

    This was everything i have ever hoped for!

    Side note: last night i had a vicious debate with a handful of ushers at a broadway show i was working about who should play Miranda Priestly in the upcoming musical. I just really dint think Patti Lupone has the subtlety for this role. We all agree that Jane Krakowski would be great, but think she would be personally offended by being cast as someone who isnt in her 20s

    • Harling Ross

      I’m holding out hope for Meryl because I revel in high expectations and extreme disappointment!

  • Charlotte Dallin

    “I personally have little-to-no interest in eating a piece of circular meat with zero gluten accompaniments, but no one ever said this lifestyle would be easy.” AMEN, HARLING!

    • Harling Ross

      that statement applies to my existence since birth

  • Sonia

    this is gold i tell ya. GOLD!

  • Harling, your MR diets are always amazing. This one was no exception!!!

    • Harling Ross

      TY LIZ

  • Samantha Lee

    Do I live in this world? How did I just realize (/you told me) that Devil Wears Prada is based off of her? Also I’ve been dying to re-watch that movie for a year, honestly, and why isn’t it on Netflix/Hulu/Amazon/anywhere???

    • Nicole

      Honestly I only realised this in like 2013 …,,

  • tmm16

    Harling, your best diet yet! Just an afterthought: You should’ve made the intern get 10 to 15 skirts from Calvin Klein while she was getting you Starbucks, but don’t specify which skirts (duh), and if she asks, simply say:


    • Harling Ross

      instead I said that to Yvonne when she asked me how my day was

      • Yvonne Dunlevie

        This is true

  • asking for raw turkey was my favorite part.

    • Harling Ross

      mine too

  • Imaiya Ravichandran

    “By all means, move at a glacial pace,” I whisper to the rainbow wheel of death that appears in lieu of my cursor. “You know how that thrills me.”

    i am…shook….

  • Annie

    oh my god… this is HYSTERICAL. just loled at work <3

  • Jackie Homan

    laughing so hard at all of this, esp. the harry potter text

  • Isabel

    The text from your friend is perfect, you can just imagine her train of thought departing from Platform 9 & 3/4.

    • Harling Ross

      excellent reference

  • LOL! This would so be me if I did an Anna Wintour, I don’t think I’d last a day.

  • Hellbetty666

    This was beautiful I am definitely going to channel Anna W at work today.

  • Grace Birchall

    Oh mate, this was amaze. I wish I could be at that stage in my life so be so cold and demanding of my inferiors. PS everyone should wear sunnies indoors

    • crtfly

      Acquire migraines. You will be wearing sunglasses all the time out of necessity.

  • Ashley Alt

    Love this

  • haha your photos and responses are amazing! <3 This is such an interesting blog post! Would love to see more stuff like that.
    Kinga xx

  • Elizabeth Sankey

    My sister worked for Anna and it’s ALL TRUE (mostly)

  • Frederikke
  • CS

    This just makes me long to relive the day when I saw Meryl Streep and her daughter Mamie Gummer sitting on a bench in the Financial District and realized Meryl was wearing a horse-riding helmet-type contraption on her head. A disguise, maybe? Didn’t work – the police officer across the street seemed really into his role as fake Meryl body guard, lols.

  • Jessyca Taef

    New life plan : Pretend to be Harling Ross pretending to be everyone else