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Anna Wintour MasterClass Review: Creativity and Leadership

Do you want to learn more about fashion and leadership from the iconic Vogue editor? Check out our honest review of Anna Wintour’s MasterClass and make sure it’s the right choice for you.

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Anna Wintour Teaches Creativity and Leadership: Our Verdict (2023)


4.3 / 5

Anna Wintour’s MasterClass provides an in-depth look at the leadership philosophy of one of the most iconic artistic directors. As an Editor-in-Chief of Vogue, Anna Wintour has plenty to say about editorial decision-making, evolving a brand, and leading with impact. Although it may not be everyone’s cup of tea, her MasterClass offers useful tips and guidelines for young designers, editors, and journalists.


  • Learning from a renowned fashion editor
  • Versatile content
  • Engaging lessons


  • Lack of relatable content

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Honestly, I wasn’t sure about Anna Wintour’s MasterClass. I’m not fond of her ignorance toward issues that her fashion empire supports, nor does her personality sound appealing. I’m sure she didn’t earn the nickname “Nuclear Wintour” for no reason.

However, I have respect for that woman. Her success is not an excuse to tolerate her choices, but it’s proof of her exceptional business and leadership skills. And I’m always curious about what such people have to say about work, creativity, and life in general.

In other words, I was intrigued by Anna Wintour’s MasterClass, and I wanted to know how my opinion of her would change after taking it.

I’ll tell you all about my learning experience in this review – the good side, the bad side, and the final verdict.

Table of Contents

What is the Anna Wintour MasterClass?

Anna Wintour teaches Creativity and Leadership” is an online course offered by MasterClass, a subscription-based platform known for offering video-based classes taught by renowned experts.

Anna Wintour has served as Editor-in-Chief of Vogue since 1988. She is hands down one of the most popular fashion editors of all time, known for her trademark bob haircut and dark sunglasses, a keen eye for fashion trends, and a demanding personality.

Although she has been the subject of much criticism, Anna Wintour obviously has the knowledge and skills necessary to run the world’s top fashion magazine. That said, her ultimate leadership tips can benefit anyone interested in pursuing a career in fashion or journalism.

There are 12 lessons with a duration of 2 hours and 36 minutes in total. Compared to some other MasterClasses, the course is not very long. Nevertheless, it covers a lot of ground, offering an in-depth look at Anna’s approach and some behind-the-scenes moments.

Who is Anna Wintour?

Anna Wintour is a British and American media executive and an Editor-in-Chief of Vogue. She has also served as Global Chief Content Officer for Condé Nast since 2020.

Wintour became interested in fashion as a teenager, and her father, Charles Wintour, longtime editor of the British newspaper The Evening Standard, would consult with her on how to make the paper more appealing to new generations. She began her career at British magazines and then moved to New York.

Due to her leadership skills, unapologetic personality, and eye for emerging fashion trends, Anna Wintour has become one of the most powerful figures in the fashion world.

Her work and approach have been the subject of criticism, though, mostly because of her elitist and unattainable views of femininity and the use of fur. However, Wintour is still in a position of power despite the rise of cancel culture. How much longer will she be able to hold the fort remains to be seen.

What is the target audience for Anna Wintour’s MasterClass?

Anna Wintour’s class covers a variety of topics related to fashion and journalism, from finding your voice to management tips and editorial decision-making secrets.

The course also contains behind-the-scenes clips that will give you an exclusive look at Anna’s meetings and the organization of Met Gala events.

Therefore, this course is great for aspiring fashion editors as well as anyone who admires Anna’s work and Vogue magazine. In fact, it’s a treat for any fashion lover.

However, it’s important to point out that Anna’s class doesn’t include specific how-to guidelines for editors – it’s more like a portrayal of her own life, philosophy, and principles. She gives away her secret to success, but that secret remains somewhat vague.

Either way, some of the people who would benefit the most from her class include:

  • Aspiring editors, designers, journalists, and photographers
  • People who want to build a brand
  • Admirers of Anna’s work
  • Fashion enthusiasts

What does Anna Wintour’s MasterClass cover?

Anna’s MasterClass is called Creativity and Leadership. That being said, the focus is not so much on fashion as on the leadership skills necessary to succeed in the fashion business.

For Anna Wintour, that’s what fashion is – business. Certainly, she is passionate about her work and fashion, but her mind is clearly focused on leading with an impact, which is not quite the same as leading with passion.

Nevertheless, in this course, Anna provides what seems like honest advice. She talks in an understandable and open way, and although some parts seem fairly distant (unless you’re in the Met Gala organization), she manages to deliver engaging and insightful lessons.

In a way, Anna’s MasterClass feels like a documentary. But at the same time, it gives young editors and designers with big dreams a lot to chew on.

To give you a better idea of what to expect from the course in terms of content, here is a quick overview of all the lessons:

  • Lesson 1 is an introductory lesson where Anna talks about her career, influences, and what fashion means to her.
  • Lessons 2-3 contain Anna’s management tips and tools that can help you find your voice and succeed in the fashion industry.
  • Lesson 4 provides a closer look at Anna’s leadership and work at Vogue.
  • Lesson 5 is dedicated to editorial decision-making.
  • Lesson 6 offers a look at the creation and organization of the Met Gala.
  • Lesson 7 includes Anna’s thoughts on photography and modeling. She also explains what it means to be a Vogue girl.
  • Lesson 8 is focused on branding and the way you can make your work stand out from the crowd.
  • Lessons 9-10 offer a look at the world of fashion design. Anna explains what she looks for in a fashion designer she wants to collaborate with.
  • Lesson 11 is a case study lesson where Anna talks about three of her most important influences and role models in the industry.
  • Lesson 12 is the last lesson, where Anna gives her final advice and explains what it means to lead with impact.

My favorite lessons from Anna Wintour’s MasterClass

I must say I’m glad I took Anna’s course. It showed me a world I’m not very familiar with: the world of high fashion, runways, and world-renowned fashion shows.

It was also fascinating to see what’s happening behind the curtains of the world’s top fashion magazine. I don’t think there are many clips online that show Anna Wintour’s office and allow you to be a fly on the wall during her meetings.

Therefore, it’s hard to pick the best lesson, but here are some of my personal favorites.

Getting the work done: Anna’s management tips

Anna Wintour sharing insights on her management methods
Anna Wintour discussing her management methods

In this introductory lesson, Anna Wintour primarily talks about what it means to be a leader. According to her, the most important thing is to have a good team of people you can rely on.

She also emphasizes the importance of feedback.

However, the most interesting part of this lesson is where she describes her typical day.

Editorial decision-making

Fashion editor emphasizing the importance of selecting controversies wisely
As a fashion editor, it’s important to choose your controversies

This lesson introduced me to Anna Wintour’s approach and methods on a deeper level. She is obviously an impactful leader, and she is not afraid to make mistakes. You have to own your mistakes, she suggests.

Also, one of the things that has kept Vogue relevant all this time is Anna’s ability to make controversial yet thoughtful decisions from time to time. She mentions the Kim Kardashian cover as an example of doing something interesting and unpredictable.

Executing a vision: transforming the Met Gala

Behind-the-scenes glimpse of the world's biggest fashion event, the Met Gala
Behind-the-scenes of the biggest fashion event in the world: the Met Gala

This lesson took me behind the scenes of the Met Gala. I was always fascinated by the relevance and popularity of this event – it’s a real cultural phenomenon. That said, it was interesting to see how Anna got involved in the event in the first place and how she helped it evolve and become what it is today.

How much does the MasterClass cost?

MasterClass is a subscription-based learning platform, so it’s not possible to purchase courses individually. If you want to take this MasterClass, you have to become a subscriber.

The standard annual plan has been renamed "Plus" and is available at $120 a year (which makes it $10 per month, billed annually), and now provides access to all MasterClass courses on two devices instead of one. The Premium plan, providing access for up to six devices costs $240 per year.

A MasterClass subscription gives you unlimited access to a catalog of 200+ classes, so if you want to take multiple classes throughout the year, the subscription is definitely worth it, and there are pleny of interesting courses on related topics to explore.

Also, the platform offers a 30-day satisfaction guarantee, so if you’re not happy with your learning experience, you can request a full refund.

Note that the "Standard" membership, priced at $72 per year, only gives you access to their short-form learning content – none of their full MasterClasses are included.

What I liked about Anna Wintour’s MasterClass

All things considered, I enjoyed Anna’s class. I think it’s insightful and engaging, and it delivers exactly what it promises: Anna Wintour’s leadership tips.

On the other hand, it’s hard to dismiss all the criticism around her leadership style and work. But if you look at this class purely as a source of information and inspiration, you’ll be able to get many benefits.

Here are some of the reasons why I would recommend this course to anyone interested in fashion.

Learning from a renowned fashion editor

If you want to pursue a career in fashion or journalism, you’ll need to be patient and find a way to stand out from the crowd. And you’ll need to be prepared for the situations that will try to knock you down.

And that’s what Anna teaches you – how to recognize your strengths, deal with criticism, own your decisions, and climb your way to the top without apology.

Learning from Anna Wintour is certainly an amazing experience for any aspiring editor and designer.

Now, are there other (less controversial) designers who can equip you with the necessary knowledge and skills? Yes. Do they have Anna Wintour’s experience? Probably no. 

After all, the subjective nature of MasterClass courses is simply something that comes with the package. This is not a creativity and leadership course; this is Anna Wintour’s creativity and leadership course.

Versatile content

In terms of content and structure, this MasterClass is really well-made. There’s a frequent change of scenery – from 1-to-1 classes to meetings and clips – so I didn’t get bored at any point.

Also, Anna talks about her experiences as well as fashion in general. She also mentions some historical facts and anecdotal stories from her rich career.

Engaging lessons

Due to Anna’s stories and the versatility of the content, lessons are very engaging. I was focused and interested the whole time, even though I’m not a fashion expert, and some of the things she was talking about felt very distant to me.

Whether you like her personality or not, Anna Wintour did a great job of teaching this class. She speaks in a clear, understandable way, and she manages to keep things concise and to the point.

Drawbacks of Anna Wintour’s MasterClass

Although I generally enjoyed the course, there are some things that could be better.

Lack of relatable content

Anna Wintour is a fashion icon, a legendary editor, a famous leader… And that’s not an easy title to carry.

Another thing that’s really hard is to find that type of person relatable.

Although they’re fun to watch, Met Gala behind-the-scenes clips only make things worse. Her advice may be applicable to other types of work as well, but if there were more general guidelines and theory, the course would perhaps be more relatable and helpful to a wider audience. 

Criticism and controversies

As you see, I didn’t mention the criticism and controversies that surround Anna’s name as a disadvantage of this MasterClass. That’s because I believe this is not really relevant here.

This doesn’t mean I’m not aware of Anna’s questionable methods and leadership style. As I explained in the introduction, I was fairly skeptical. Yet, I decided to take this course with a relatively open mind and decide whether it’s worth taking.

And honestly, I think it is. You just need to approach it in the right way.

If you want to see what’s happening in Vogue meetings and inside Anna’s head while she’s making editorial choices, this is a course for you. Is that a truthful representation of how things really are over there? I doubt it.

This MasterClass is obviously designed to show Anna in the best light possible. Throughout the course, she is kind, friendly, conscious, and almost relatable. She talks about the importance of diversity in fashion and the representation of women as if she’s never been involved in any of the controversies.

It looked as if she was trying to fix her image.

Well, she said it herself: you need to be a part of the conversation. And if the world wants you to be more conscious and inclusive, that’s what you have to become.

But I didn’t expect anything else from her MasterClass. We’re talking about an online course, and her role was to convey knowledge. And that’s what she did quite well. Now, whether you want to take her advice despite all of this is up to you.

In my opinion, it’s possible to benefit from this course while taking some of her advice and stories with a grain of salt. 

Review conclusion: Is Anna Wintour’s MasterClass worth it?

To sum things up, I don’t regret taking Anna’s class.

This course allowed me to discover more about what’s going on in the Vogue meeting room or behind the scenes at the Met Gala. It also gave me a closer look at Anna Wintour’s leadership philosophy.

I probably didn’t get an honest picture of how things really work in Anna’s office, though. I still believe some of her choices (like promoting fur) deserve to be criticized, and I do question her motivation to change; she wants to stay part of the conversation, after all.

But one thing is for sure: she is experienced, skilled, powerful, and unapologetic, and she is the right person to talk about leading with impact.

Now, whether you should take Anna’s class or not depends on your personal preferences and expectations. If you’re here to write down management tips and expand your knowledge about one of the most prominent fashion magazines in the world, I don’t think you’ll regret it.