Business, Politics & Society

Evolving a Brand: A Look Back at Iconic Vogue Covers

Anna Wintour

Lesson time 20:22 min

Anna delves into the Vogue archives to discuss a number of her most famous, iconic, and memorable covers. She breaks down her decisions and how those decisions helped evolve the Vogue brand.

Anna Wintour
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ANNA WINTOUR: As a leader for your company, you will be tasked with making larger strategic creative choices that help evolve how the audience-- the public-- understand your brand. Your brand has to be at the core of all your creative decisions. What is it, what does it stand for, and how do you move it forward? I've picked out some covers to give you some insight on how I have made some larger decisions on behalf of Vogue over the past 30 years that has kept it as a leader in the publishing and the fashion industry. [MUSIC PLAYING] So this is my very first cover during my editorship at Vogue. It was of a wonderful young model called Michaela, whom is from Israel. And this was not actually photographed as a cover. So always remember to expect the unexpected and not always to be locked into your way of thinking. Sometimes surprises are best. This was a shot that was photographed for inside the magazine. It was at a time when Vogue was only showing iconic Richard Avedon cover pictures of models. Very tight cropped, big jewelry, big smile. And it was very much at a time when the belief was the girls always had to be looking directly at the camera. It was time to do something different. Otherwise, why was I there? So I think when you are making a big change, it's always important to remember that people expect change. They want change. They are looking for change. They may not know what it is but it's in the air. When this shoot came in, the whole shoot was absolutely enchanting and lovely and full of energy and very immediate in its attraction that I thought that this would make a great cover. And the powers that would be were a little bit surprised. The printers even questioned this picture. But it made a statement. It made a statement that it was a different time. We had a different view on fashion that we wanted to be much more accessible, much more free. It almost had an Instagram feel about it because it was shot in such a spontaneous way. And the eyes were not completely open. They were actually almost closed. She was wearing amazing, amazing couture T-shirt by Christian Lacroix with the cross embroidery and a pair of jeans from Gas. And we actually asked Gigi Hadid to mimic this cover because it has become such an iconic cover for fashion followers throughout the world. It was recently that we received a lovely letter from the model that we used on this cover, telling us about her-- her current state. And she is married. I think she has many children. She is a psychologist. But this remains for her, as well as for us, a landmark moment. [MUSIC PLAYING] So for my very first September issue, I had decided to put Naomi Campbell on the cover because to me she represented everything that was happening in fashion at that time. She was beautiful. She was fun. She loved fashion. She was every designer's favorite model. She was a girl of the moment to the n-th degree. And at that time, when you worked at Con...

How to be a boss

A fashion and media icon, Anna Wintour has been driving our cultural conversation for more than 30 years. The Vogue Editor-in-Chief and Artistic Director of Condé Nast takes off her signature sunglasses and gives you unprecedented access to her world. See how Anna nurtures talent, makes bold decisions, and evolves a brand. Learn how to lead with impact from a visionary creative leader.


Students give MasterClass an average rating of 4.7 out of 5 stars.

This woman is truly inspiring. And the definition of calm, mindful, strong leadership.

Anna's class has been me the extra push in other directions to bring into play with my own Magazine. Many new ideas/ processes to try out (some are already in motion) and I can't wait to see what comes of these new ideas. Thanks Anna! x

I sat dow at my desk to meet Anna. This is a milestone to set my plans on following my dream career as a fashion creative. Thanks Anna for sharing your thoughts. I'm certainly going to Starbucks now!

This was RIVETING! Anna is such an inspiration and finds such JOY in all that she touches. It is a must for ANY one who wants to create, lead and inspire! Can't wait to watch it again!



I'm in my mid 50's and am pursuing a career I've dreamt of doing for decades. Although I've worked on projects independently and collaborated with Architects and Interior Designers, I am now leading a team that is working for me. I'm very pleased with how my first custom home is coming to a close, but I've lacked the leadership in how owning my decisions are best conveyed, especially with our young designer. Anna's Master Class has opened my eyes as to what it is I need to pay more attention to. I love Anna's management style and her tips that will clearly define my next build from conception to completion.

Abbey T.

i am lost.. i cant seem to resume on a pc but i can resume when i am on a tablet.. goes for all classes .. why

PAmela K.

This was fabulous. I am an older woman having to start over and I found her lessons more helpful and concise than a hundred self help books! I had no expectation that Anna would be My new role model! Every sentence she spoke was bursting with wisdom and common sense. She is a revelation!!! Pamela from Texas

Victoria M.

This class about photography and images was excellent! I’m still learning how to communicate visually so it was full of great tips for me.

William S.

You're very intelligent Anna and a joy to watch. It would be nice to see Melania Trump on the cover. It's probably about time.

Linda G.

Anna Winter, your class exceeded my expectations and that is saying a lot! The points you made are so important, I could relate to the personal and professional experiences in my life. Hearing you speak was also reaffirming. Presenting creative ideas and following your inner compass may not always be a popular approach but it has always proved rewarding to me in the end.

Brett G.

This lesson is super helpful for when I start my neighborhood fashion magazine (rolling eyes). The Vogue documentary continues...

Lito M.

Full of great idea's, amazing creativity. The vision putting in reality are best.

susan R.

I felt Anna was noticeably more animated and enthusiastic in this session. Photography and it’s messages are clearly a passion.

Lynnemarie S.

Enjoyed the look back at the many covers. As a writer I enjoy learning the back story of the covers she has chosen to share.