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Anna Wintour: The 6 Lessons I Learned from the Vogue Editor

Anna Wintour: The 6 Lessons I Learned from the Vogue Editor

Anna Wintour in a clip from the documentary “The September Issue,” a story of the magazine preparing for its 2007 fall fashion issue
Image from IMDB

Anna Wintour has become a household name, but my fascination with her didn’t happen until recently. It started with a binge-watching session on YouTube. You know how it is: a thumbnail catches your attention (Miranda Priestly with hand-drawn devil’s horns, and an ironic statement that says, “She’s Perfect.”) and down the rabbit hole I went. I ended up watching all “Go Ask Anna!” videos on Vogue’s channel, clips of “The September Issue,” and other interviews and biographies dedicated to her.

Influential, trendsetter, kingmaker. Decisive, demanding, and at times terrifying. Anna Wintour is an enigma, and I’ve picked up several things from her, which I think are worth sharing to all Modern Filipinas.

1. Sometimes you need to dress the part.

“Anna Wintour Talks Rihanna’s Designs, Flip-Flops, and What People Get Wrong About Fashion” (video mark: 3:10) “I am not sure that I approved.” He now works at TV Guide.

We’re in a time when self-expression and uniqueness are celebrated. It doesn’t mean, however, that we are entitled to turn our noses up at “conventions” and be stubborn in doing things our way (or else). Are you really making a stand or breaking the rules just for the sake of?

A war cry isn’t necessary for every little thing, and sometimes doing what’s expected of you is an act of courtesy. Nothing more, nothing less. So when you’re invited to a black-tie event — oh, like, the Met Gala, for example — and you arrive wearing a casual dress, expect your boss to raise an eyebrow at your outfit choice.

2. Rumors. That’s all they are until you prove them right.

On “73 Questions with Anna Wintour” (video mark: 5:14) Q: What’s the least true rumor about you? “They’re all true,” Anna says with a cheeky smile.

I’m sure Ms. Wintour has many detractors, but I get the impression that most of them will still smile to her face. Her attitude toward the rumor mill, for me, is inspired. She’s glib with shallow questions, but forthcoming when people come to her with sincere curiosity. She’s shown us that no matter what people say about your character and work ethic, they will stay rumors until you validate them. You may have no control over what’s said about you, but you can control how you respond to them.

3. Rethink dressing in all black.

On “73 Questions with Anna Wintour” (video mark: 2:15, 3:50) “Virginia. Where’s the color?”

If you watch enough Anna Wintour videos, you’ll notice that she loves to wear color. Very rarely do you see her in somber shades (with the exception of her, ahem, sunglasses), which is why it’s unsurprising that she considers head-to-toe black a fashion faux pas (in fact, she mentions this twice in Vogue’s 73 Questions with Anna Wintour). Although Ms. Wintour’s personal style preferences aren’t fashion laws, I think she has a point. If wearing all black is making you fade in the background, a pop of color might draw the attention you deserve.

4. Invest in people who’re worth it.

On “Stylist Kate Young: From Anna Wintour’s Assistant to Transforming Selena Gomez” (video mark 4:13) Learn to recognize aptitude, in yourself and in others.  

On the Hollywood Reporter’s Magic Hour feature on Kate Young, a former assistant of Wintour’s and now a successful celebrity stylist, we learn that Vogue’s matriarch doesn’t leave everything up to HR. “I insist on interviewing all the assistants,” she says in the video, “because we’re going to invest… time and training.” This also sheds light on her perspective as a boss: train your subordinates so that they can get promoted. If you feel your boss isn’t investing in you, well, you should know that you deserve better.

5. “No,” is not an answer.

On “Stylist Kate Young: From Anna Wintour’s Assistant to Transforming Selena Gomez” (video mark 6:50) There’s no tapping out in fashion and in life.

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The author of the best-selling novel-turned-hit movie, “The Devil Wears Prada” said the iconic character of Miranda Priestly is based on Ms. Wintour. If that’s not enough indication of how she is as a boss, Kate Young can give you more insight. She says that while working for Wintour, she learned to find seven other ways to accomplish a goal if the path you wanted to go on proves impossible. “No is a cop-out, there’s always an alternative,” Ms. Young says.

6. Trust your instincts. But own up to your mistakes.

BBC News, 2011 (video mark: 4:00.) Wintour leads fashion not because she knew everything, but she went to places no one dared to before her.

Use facts to inform your decisions; but if your gut says otherwise, take the leap. There’s no guarantee of success every time, and you’ll have to own your mistakes (and learn from them) when they happen. However, when it turns out you’re correct, then you might just set a new trend. The best part about taking risks is you won’t be up at night regretting missed opportunities and dreaming about the what-ifs.

After watching the interview above, it comforted me to know that the woman considered to be the most powerful in her industry didn’t have everything figured out at the beginning. She grew into her role, and she made the industry grow with her. It’s an inspiring and empowering thought for every Modern Filipina.


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