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Design & Style

Case Studies: Lessons From Creative Leaders

Anna Wintour

Lesson time 09:58 min

Telling the stories of Christopher Bailey, Miuccia Prada, and Michael Kors, Anna highlights what has made these creative leaders successful.

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.


[MUSIC PLAYING] ANNA WINTOUR: I'm going to share with you things that I have learned from some of my very favorite designers. Even though they are designers specifically, each has a lesson that is relevant for you to know and understand as a creative leader no matter the type of work that you are engaged in. [MUSIC PLAYING] There are so many designers whose paths I admire and respect and have followed over many years. But if I was to think who would be the most helpful possibly to all of you, I think I would start by talking a little bit about Christopher Bailey at Burberry who left college and went to work for a number of famous designers like Donna Karan in the United States and then Tom Ford at Gucci before he was brought in by Rose Marie Bravo to become creative director at Burberry. And because Christopher had, I think, a good 10 years experience working for some of the biggest and most brilliant names in the business, I think that he not only had a very sure sense of who he was and what he wanted to do with Burberry, he had real experience. And I think it's very, very important to remember that the designers that leave college and go straight into creating their own businesses and succeed are actually few and far between. And my advice to all of you is to really think very carefully about working for a designer whose work that you admire before you start your own business. So Christopher went to Burberry. And because traditionally Burberry had always shown in Milan because at that time, people didn't think that London was the creative hub that it is today and that it was so-- it seemed a bit provincial. It seemed a bit quiet. And a big house like Burberry didn't think that there would be enough sparks flying or enough news being made if Christopher showed in London. So we had many dinners over the years where we talked about how unhappy he was with the idea of showing in Milan and how he didn't think that it really fit with his sensibility or his point of view, but the powers that be felt very strongly he should stay there. And he did perfectly lovely collections, created the plaid bikini on Kate Moss, really took Burberry into the mainstream, made it something that women and men everywhere wanted. But it wasn't talked about maybe the way that he might have wanted. And Christopher is a wonderful man, very humble, very polite, very low key, never puts himself forward. But finally, he had his way. And they took Burberry back to London. And it was the most important move that Christopher made during his years there at Burberry because somehow he was able to channel what was best about Burberry. He found its core. He channeled the cool, young kids in London. He channeled music. He had the shows in beautiful tents in the middle of Hyde Park. He just made it an event. And because he brought Burberry back to London, he made London exciting again, and everybody started to go. It became a absolutely you have to go on your way...

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.


Enjoyed the class and as a professional I was reminded of some important topics. Anna is a dream teacher. I highly recommend this class for leaders in any career.

Learned about the importance of have a clear vision and stay true to what your vision is, be mindful and thoughtful about how you will share your vision to your team and to the World. What an important lesson to have, thank you Anna!

Anna is a breath of fresh air...her style is flawless, full of energy and inspiring.



Success may take years with ups and down, but Be true to yourself, know your customer.

Yvette F.

Loved it. So relatable for any industry. Especially the part on how you really need to know the personas of your audience. Everything there is to know about them.

Erika Von Finck

Excellent examples of true creators and very compromise creative leaders. This is also an example of what we all can create. The simple thing to do is to choose from the heart, from your soul, to know what do you really want to do, and then, let it go, without expectations. Accept all the things as they come, no matter what, trust in it, because if you push it, this energy will surround your creation and it will delay it. Your creation will come at the right moment, just don´t stop to work on it. If it´s for you, it will come, if not, your soul will get you to the right path. But most important, don´t stop to trust in yourself and in your creation, no matter what. Can you do that?

A fellow student

Knowing your audience is so critical across all forms of business and mediums.

Sheryl B.

Anna's feedback to the new designers is so supportive, true and trusting. Chapter 10 provided a foundation to someone and many that you should always present your true self. I share that same thought to my students.

Lorena (Lorraine) P.

Anna highlights what has made these creative leaders successful which is very important to know for our leadership.

Richard H.

Three amazing creative leaders in the fashion industry. Anna does a great job highlighting them.

Alexandra L.

Inspired people are inspiring. More than a class, a testimony of engagments that gives you the will to fight for what your heart tells you is wright. Let's go for it!

A fellow student

I liked this and found it valuable, Anna. Thank you to yourself and MasterClass.

Carolyn S.

More exquisite details from the INSIDE of the fashion industry. I do think new designers need to consider using sustainable materials to battle climate change and the degradation of our environment. Fashion has a huge impact on our planet. Hemp Silk is gorgeous ... I loved one of the Vogue Fund finalists who actually used vintage fabrics and transformed them into brilliant fashion designs. [An artwork/collage I did in the theme of what is old is new again - and wearing nature]