I Lived Like Anna Wintour For A Week And It Was So Empowering
Walking in a Wintour Wonderland. At the Met Ball we can build a snowman. And pretend it’s Karl Lagerfeld.
I’m not exactly Vogue material.
I am a sunshiney, helpful person, but also a loudmouthed drama queen who swears like a sailor and eats like a fraternity brother. In discerning my career, I have both almost been a nun and almost been a WWE Diva. My friend describes my fashion style as “Overly-Excited Third Grader.” I mostly wear free T-shirts, yoga pants and sneakers because I like ACTIVITIES (like nachos and Pinterest…).
Despite my soft spot for Chipotle and moccasins, I have always admired Vogue editor-in-chief Anna Wintour. She’s the epitome of power and influnce, with a low-grade volatility always simmering just below the surface. Each year, she serves as chair of the Metropolitan Museum of Art’s annual Costume Institute Gala, which is basically celebrity prom.
Who is Anna Wintour?
Besides being editor-in-chief of Vogue, Anna Wintour is also Artistic Director of Condé Nast and the inspiration for Meryl Streep’s intimidating fashion editor in The Devil Wears Prada. She is the heart and soul of the fashion industry, setting trends and bringing newb designers into the game. Not only is she a powerful figure in fashion, she’s also a powerful lady-guru type who pushed Blake Lively to start her own fashion line and told Kimye, “North is a genius name.” Wintour has used her influence to feature some of the world’s most respected female trailblazers in the pages of Vogue?—?among them, Malala Yousafzai, Hillary Clinton, and Sheryl Sandberg.
She writes about the power of fashion to shape culture the way people in my generation talk about the life-changing magic of Harry Potter and Beyoncé.
If Anna went to Hogwarts, she’d be a cross between Ravenclaw and Slytherin, because she is brilliant and ambitious, but often comes off as cold and apathetic. She’s the total opposite of me in every way. In a culture obsessed with life hacks, her morning routine is the most popular and most studied on Pinterest. So, I decided to copy Anna Wintour’s daily routine and the habits she looks for in her employees for a week to see if I would become more productive, more confident, and obviously, more fashionable.
DAY ONE: I become Anna.
The morning started off with a 5am wakeup, which was surprisingly not terrible. Except I forgot to tell my roommate that I was in the process of becoming fashion’s most feared personality. When my alarm went off a full 2 and a half hours before it usually does, she woke up screaming. +5 Wintour Points for inspiring fear in others, something Anna does with great finesse.
Anna plays an hour of tennis every morning. I am nowhere near a tennis court, so I looked up the amount of calories burned during one hour of tennis and hit the elliptical to burn the equivalent amount.
It was DEFINITELY the most productive workout I’ve ever done because I usually just show up and try my best. This workout was much more focused: Burn 350–400 calories in less than an hour, GO!
Every morning, Anna has a blowout and gets her makeup done by professionals. Her annual hair, makeup, and clothing budget is around $200,000. Mine is around $82.
I haven’t used a blow dryer since like 6th grade because my friend burned her hair off with one and that scared me away from them. But I tried my best, and once my hair was dry, I straightened it, hoping to emulate Wintour’s ultra-sleek look: the iconic bob with blunt bangs, the same hairstyle she’s worn since she was 15.
Unfortunately, my hair resisted and maintained its scraggly Chewbacca-like texture. I tried to copy her makeup style, which is very light and neutral and not easy to screw up. The makeup felt like an exercise in futility, though, because most of it is concentrated around the eye region, and therefore concealed by the huge Chanel sunglasses that are Anna’s signature look. And you betcha I wore sunglasses 24/7, too. From H&M.
One of Anna’s big fashion requirements is to dress in color and wear a necklace, and I tried to style my look based on that; I wore a light pink and navy splotched (idk design terms? flowery-shape things?) dress. I even wore blue and white heels. Anna is also really big on necklaces, so I wore this pearl necklace I stole from my 10-year-old sister. I think she got it from Claire’s.
Surprisingly, I was really self-conscious about my appearance. I felt like I was showing too much skin, to the point at which I scouted out a stapler and stapled my dress so it showed less cleavage. I also wished I had worn leggings, even though the dress went past my knees. Overall, I felt very exposed.
Belowdecks, my feet were KILLING me because heels are the absolute worst. Anna’s own daily uniform requires a pair of Manolo Blahnik slingbacks that the designer has produced exclusively for her for twenty-two years. The style even bears her initials: AW. I know I will have truly made it someday when a prestige designer produces one style just for me, with my name on it. Let’s be real, though, my slingback equivalent is a double-carnitas Chipotle burrito (no rice, no beans). Someday they’ll call it the “KM” and it’ll be on the secret menu.
My coworkers didn’t seem too surprised that I wasn’t wearing my usual grody outfits. One told me I looked like Jackie O, which was so kind and made me have this “Shit, people are looking at me!” moment. The one element that threw people off were the sunglasses. I really committed to the sunglasses, wearing them indoors, all day long.
DAY TWO: I slum it at college.
I am a full-time college student (with two majors, a minor, a student club to preside over, and two jobs. COME AT ME, BRO). As I went about my day?—?attending class, studying at the library, Snapchatting the adorable bunnies that hop around campus?—?I felt super fancy and noticed I was sitting up straighter. I strode around, strutting rather than slumping. I felt like a boss-ass bitch.
My friends DEFINITELY noticed my fashion change and did not like what they saw. One said, “Ew, take those glasses off! You look like a soulless Stepford wife.” Another chimed in and said that I looked nice but that the sunglasses-all-the-time made me appear “disenchanting and creepy.” I told them that is not how you speak to Nuclear Wintour. They were both flabbergasted when I left lunch after 7 minutes, which is how long the average meeting at Vogue is. Anna is calm and aloof in conversation, whereas I am very excited and down to earth, so my friends were also very thrown off by my short, clipped responses.
Two of my professors did not notice that they were in the presence of a DIVA, and my Christian Philosophy professor saw me strut into class and said, “Well you look quite astonishing today. What do you think about artificial intelligence and the ethics implied by our research of it?” Um…okay…
In all of my classes, I was suddenly being called on the most even though there were plenty of other students raising their hands. My professors also seemed to be taking me more seriously than usual.
While my teachers treated me like a damn genius, my classmates were more skeptical. When working on a group project, someone felt the need to repeat the instructions to me four freaking times before I snapped, “I fucking get it!” And even though Anna Wintour would have probably taken my side in the argument (because the girl was wasting meeting time, which is a big no-no at Vogue), I still felt like a huge jerk. But it also made me consider that you can’t let people walk all over you if you truly want something to get done.
DAY THREE: I eat like an icon.
I don’t think anyone would be surprised at how restrictive Anna Wintour’s diet is as she is a skinny lady extraordinaire. I loosely attempted to copy it calorie for calorie in order to get the full experience. To be honest, I assumed it would be a bullshit supermodel diet that’s like “For my cheat meal I lick a melting ice cube,” but Anna Wintour’s diet is very nutritionally dense and keeps you full all day long.
Breakfast is smoked salmon and scrambled eggs with a Starbucks latte. The only place I knew of with smoked salmon was Einstein Bros. Bagels, so I got a nova lox bagel with eggs on it. I’m sorry, Anna, but I couldn’t let a perfectly good bagel go to waste. Fun fact: Smoked salmon is probably the most disgusting thing I have ever put into my garbage dump of a body.
For lunch, Anna either has a bunless (more like funless) hamburger or a rare steak and a mixed greens salad with no dressing. I can’t afford that, so I just got a steak salad WITH dressing because I’m a child and VEGETABLES are GROSS.
Holy protein, Batman. Even with my slight variations, I had 35 grams of protein with breakfast and 40 grams of protein with lunch. I couldn’t imagine how much more I’d have consumed if I had followed the diet PERFECTLY, with a ribeye steak and the proper amounts of smoked salmon and eggs. To put the diet into perspective, that’s the same amount of protein that many professional athletes and body builders consume. All for one tiny little fashionista who likes to play tennis.
DAY FOUR: I culture.
At this point in the week, I was pretty used to the Anna lifestyle, so I stepped it up a notch. Anna wants her Vogue employees to be cultured, advising them, “You have to go out and see things?—?screenings, theatre, exhibitions.” One of the first questions she asks in interviews is if you’ve been to a museum lately. So, after class one day, I wandered through Chicago in pursuit of a museum. I went to three different museums and they were all closed (Anna probably would have checked the hours of operation ahead of time, or more likely, had an assistant check for her). However, I did manage to view some pretty fantastic public art, like the Bean in Millenium Park. I mean, art is art, wherever the hell it is.
I wandered around some more, until finally stumbling upon a screening of the Irish documentary “A Terrible Beauty.” Success! I am now “cultured!” While I sat in the dark theater watching Irish revolutionaries and British soldiers go to battle, I could not help but wonder why the hell watching this movie would make anyone a potentially better candidate for Vogue. However, an evening wandering around looking for museums and watching a pretty cool documentary is better spent than going home to play Candy Crush and watch “60 Days In.”
DAY FIVE: I fashion real hard.
At this point, I have worn literally all of my clothes that are not T-shirts and sweatpants. An intervention is long overdue, so I head to a clothing store to find an outfit that I think Anna would approve as something colorful but chic and smart.
I really loved this dress; plus it was floral print, noted as a favorite pattern of Anna’s. My favorite part about it was that it was on clearance AND part of a “buy one, get one free” deal! Usually when I look for clothes I get pissed off and just grab something loose and black that I can hide inside during whatever function is forcing me to wear it. This experience was a lot more fun, partially due to the joy of spending $50 on $120 worth of clothes.
I spent the rest of the day reading Vogue, because there weren’t any other Anna things left in the schedule. Vogue makes other fashion magazines look like a 6-year-old wrote them in crayon. Anna’s inspiring touch is evident throughout the magazine, but most especially in the Editor’s Letter, in which she writes heartfelt commentary about how fashion is evolving and adapting. This excerpt, from the January edition, describes the Spring 2016 fashion trends as:
…at once liberating and energizing, a triumph of optimism and individualism…the huge shift away from the superperfect, supermatched, and superpolished toward what can only be described as imperfect, human-scaled beauty.
The average 20-something categorizes fashion into two categories: comfy and sexy. But Anna doesn’t see fashion as just clothes?—?she views it as the marriage of art and commerce, and as an industry that fuels national economies and employs thousands of people around the world. Additionally, her personal appearance isn’t super crazy (very simple hair and makeup) because she wants all attention on the clothes and designers she is wearing.
The Wintour Forecast (or, How My Week As Anna Impacted My Life)
I capped my week as Anna with a fashion show, which you can read about here.
Livng in Anna’s bespoke shoes for a week was no small task. So, what did I learn from the experience?
Was I more fashionable? Well, obviously, yes. I dressed more like an actual adult and less like an overly-excited third grader.
Was I more productive? 100% yes.
Was I more confident? Yes, and in ways that were markedly different from what I had expected going into this experiment. At the outset, I had been anticipating a boost of confidence in my physical appearance alone. But it was more than that. The famous sunglasses WORK because they really do feel like a shield in front of your face. Emulating Anna?—?in particular, her decisivness, confidence, and take-no-prisoners truth-telling?—?boosted my confidence at work, at school, and with friends. Behind those famous shades, I felt less self-conscious and freer to be Katie, which allowed me to really leap over the walls of insecurity and get shit done.