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Design & Style

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.


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...

About the Instructor

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.

Great leadership tips, without too much focus on fashion or journalism industry. Would recommend to anyone!

i appreciate anna wintour's candour and her advice, while i'm not in the fashion industry, her lessons still apply to my work. finding my voice, using it, and staying true to it while finding ways to give back to the world is one of the best takeaways from this class!

Really great learning! I am not in the fashion industry, but found a lot of value in the content around leadership. Transferable to many other fields. Thank you Anna and Master Class for making this learning available!

I enjoyed the class. The platform itself still has some glitches in it that don't allow to pause successfully and the lessons jump back and forth all over the screen.


Sedinam Naki Adzoa A.

I for one am not in the journalism or fashion industry but these lessons are applicable to many different areas beyond those two. The principles she teaches are fundamental for every kind of leadership, you just have to know how to apply it.


In this lesson, Anna radiated joy and excitement and shared some of the backstory on covers that she adored. Embracing change yet not just to be different. The personality of her subjects.....more than just a pretty face.

Erika Von Finck

Great lesson! I totally agree that always reflect what your brand represents. You can make any decision based from that core but always try go beyond the mind, beyond what´s happening in the world, take risks, follow your heart because besides that your brand is your voice, it´s good to reflect a diversity and different energy of every result because people expect change.

Christina N.

Love the lesson and fascinating insights. However, Naomi Campbell is not African American. She's English.

Leila R.

I cannot recommend enough MasterClass with Anna Wintour. She is extraordinary, marvelous, genius person. Many thanks to all team of MasterClass.

A fellow student

Yes Anna Wintour takes risks with Vogue covers; however, the ultimate risk would be to feature our present First Lady, Melania Trump. Unfortunately, those risks discussed in this lesson, are risks that fit Vogue's political narrative. Don't forget you have a much more conservative audience. We all deserve a little bit of recognition. Melania is also an extraordinary woman who is handling the constant attacks on herself and her family with extraordinary dignity. She is as well so beautiful. Just a thought...

Lorena (Lorraine) P.

Anna is a great inspiration ! She breaks down her decisions and how those decisions helped in her career.


Anna is so inspiring! I use their knowledge everyday at work and my project

Mary S.

Awesome class! I find Anna's advice and tips very insightful. She is giving me a different perspective on Vogue and on her. Any misconceptions I might have had have been blown away. Wonderful class!

Kimberly B.

Loved the authenticity and genuine passion in this lesson, as she takes us through the history of her decisions. I always find it most fascinating to learn from people when we get a peek behind the curtain and into the thought process of leaders. That's the magic and real pearls of wisdom-the narrative and reflection.