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
Teaches Creativity and Leadership
Anna Wintour gives unprecedented access to her world, teaching you how to lead with vision and creativity—and without apology.
Get All-Access


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.

I loved hearing from such a wonderful, thoughtful and professional leader.

When you investigate each sentence, it opens new worlds and questions you have not asked yourself. Love the directness!

Loved it. So happy Anna created a MasterClass. It's the first one I've completed and I did it in one sitting. Thank you Anna for taking the time to share your wisdom with us!

I learned the vision of Vogue, of Conde Nast. I learned the vision of Anna, her rigor and consistency in her leadership, which is true to apply everywhere else.


Lorne K.

As much as I enjoy getting a glimpse into the world of high fashion with one of the great icons of the industry, this is much less a "Masterclass" than it is a quasi documentary and interview piece. There is virtually no training or lessons to be learned, merely subjective insights into the business. The only "teachings" are the note cards at the end of each lesson. She purports to take us "behind the scenes" in a few instances but there are no great revelations or secrets revealed and those scenes are heavily edited. I've taken a dozen Masterclasses so far and this is the first one that I'm truly dissatisfied with. Anna is a wonderful storyteller and very eloquent but this feels more like a vanity project than an attempt to share pearls of wisdom with the class.

Suze Yalof S.

The group cover with supermodels in shorts and cropped stripped tops is one of my favorites. I remember when Carlyne Cerf did the run through and wanted to show it to Anna so she grabbed some assistants and had us pose in the same clothes and position took a Polaroid and then brought it in to Anna’s office. It was such a moment to be there at the beginning. So many great takeaways from the class ! ⭐️⭐️⭐️⭐️⭐️

Abby G.

I really enjoy her perspective on audience. All I hear now of days is "define your ideal client." Have the passion for whatever is it and they will find you. My heart felt that one.

Robin C.

Really enjoyed the behind the scenes. As an Event Strategist I was most interested in the planning and execution of the Met Gala, however I loved all of the segments. In my role, I have to think about the customer journey, overall experience, and applying to campaigns and I see how Anna applies those similar tactics to the pages of Vogue for a larger connection.

Dounia E.

I am going to binge watch these videos until I start thinking and speaking like Anna, until I start finishing her sentences. These lessons will have a tremendous impact on my life. I think that, without knowing it, I’ve been waiting for something like this my whole life. :) Thank you Anna and thank you MasterClass

Tarik S.

Great take aways from the class I heard some common things from Annie Leibovitz in her master class as well.