Business, Politics & Society

Case Studies: Lessons From Creative Leaders

Anna Wintour

Lesson time 9:59 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.
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[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...

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.

It is a very good class. She opens up on vital points. Wish it was a bit more in depth but still for the time commitment she gave, it is good!

Far the best, "THE BEST", business leadership class I've seen! Very real loaded with substance! Anna is a powerhouse a true CHAMPION! Seen (3x) Love

Anna, gave me a really important reminder, that I must be true to myself in regards to be creative and to not let be conformed to the status quo. Thanks for helping me be more bolt and led with confidence

Interesting to hear about Anna's experience and thoughts. Especially given that she rarely talks about this in such detail. Inspiring.


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]

David S.

What an eloquent person. I’ve really enjoyed listening to your wise words. Thank you.

Alessandra C.

I'm working in science and looking into different approaches to leadership, to perfect mine. It's very helpful for me to learn from different sectors, keeping your mind open is always useful. I loved this masterclass and found very useful advices that I already started to apply, first of all the idea to make short and more effective meetings.

Anna M.

I would love to see all of your portfolios! I am a visual artist, a printmaker, who loves costume. You can find me on Instagram @annajanemcintyre or


This is great advice, I’ve always informed post grad fashion students that it’s important to build up a portfolio of experience from the real world before embarking on their own path. There is no real substitute for practical experience from brands that have already been there and done it. 💎