Anna Wintour MasterClass Review

Anna Wintour has led Vogue magazine as editor-in-chief for over 32 years. A powerhouse in the world of fashion, she is also the artistic director of Conde Nast. In her MasterClass, Anna teaches you how to build valuable skills as a creative leader and effectively manage a team.

By the end of the Anna Wintour MasterClass, you’ll gain a deeper understanding of how to lead your team with a vision and make important decisions for your brand. Covering 12 lessons in total, Anna’s course is insightful for any business-minded individual.

If you’re here, you’re probably keen to find out what’s inside this MasterClass and to decide whether it’s the right course for you. So, in this Anna Wintour MasterClass review, I’ll weigh up the pros and cons to help you decide.

But, before delving into these points, here are the highlights:

Here’s what’s in store in this Anna Wintour MasterClass review:

• About Anna Wintour and MasterClass
• Inside the Anna Wintour MasterClass
• What I liked/disliked
• Who the course is for, prices and alternatives
• What others have said about the MasterClass
• Final verdict – is it worth it?

First, here’s some basic info:

About Anna Wintour

Anna Wintour has been editor-in-chief of Vogue magazine since 1988. She’s also the artistic director of Condé Nast Publications.

Working within the Council of Fashion Designers of America, she developed and evolved the Vogue Fashion Fund. This earned her the CFDA Geoffrey Beene Lifetime Achievement Award.

As a pioneering figure in fashion since the 1970s, Anna Wintour is a force to be reckoned with in the business world.

If you’re looking to develop your skills in creativity and leadership, Anna Wintour’s MasterClass could be the course for you.

And if you haven’t seen the trailer yet, I highly recommend you check it out here:

About MasterClass

“Online lessons from the world’s best”

Founded in 2015, MasterClass is an online educational platform. Unlike other online courses, MasterClass is headlined by renowned experts in their fields. These include Gordon Ramsay teaching cooking, Bill Clinton teaching inclusive leadership, Bobbi Brown teaching makeup, Annie Leibovitz teaching photography, Simone Biles teaching gymnastics, Margaret Atwood teaching creative writing, and Martin Scorsese teaching directing.

With over 150 classes from its celebrity teachers, MasterClass is slowly altering the landscape of e-learning. It goes without saying that this is a unique opportunity to learn from some of the highest achievers in their fields.

However, I don’t think MasterClass is for everyone. In this Anna Wintour MasterClass review, I hope to highlight both the pros and cons to help you decide whether this is the right course for you.

If you want more details on MasterClass and some of its most popular classes, check out our Masterclass review and best MasterClass article.

Inside Anna Wintour’s MasterClass

Covering 12 lessons in total, Anna Wintour’s MasterClass clocks in at 2 hours 30 minutes’ viewing time. Most lessons are between 10 and 15 minutes long.

I’ve broken this course down into 4 sections:

1. Meet Your Instructor
2. Management and Team Leadership
3. Working in Fashion
4. Parting Words

As well as the video content, MasterClass offers you a 35-page Workbook, which you can download. Also, there’s the Community Hub – a forum dedicated to Anna’s students – where you can share and discuss ideas about the course.

Here’s what’s inside the Anna Wintour MasterClass.

Section 1/4: Meet Your Instructor

In her introduction, Anna discusses her upbringing during a time of “cultural revolution.” This, along with her father’s career in journalism, informed both her childhood and her future with Vogue.

She teaches you how to:

• Acquire valuable skills in different sectors
• Gain experience in fashion shooting
• Use fashion to reflect a culture
• Work your way up the career ladder
• Collaborate well with others

Starting out as an editor, Anna teaches you how to gain worthwhile experience without any formal training. She also offers a timeline of her career, including how she got into Vogue.

For Anna, brand image is crucial to your business’s success. As a result, Anna places a lot of emphasis on how to establish or evolve your brand’s values.

She summarises how she did this with Vogue (a taste for chapters to come) and lays down what you can expect to learn from her MasterClass.

Section 2/4: Management and Team Leadership

Here, Wintour focuses on how to best manage and lead a team. First and foremost, micromanaging is out the window. As she curtly remarks, “I don’t believe in it.”

Instead, Wintour shares her methods for time management, leading your team through active engagement, and making difficult decisions.

Getting the Work Done: Anna’s Management Tips

As Anna puts it, “a good team is everything.” As a leader, it’s your job to manage and motivate your team. Here, she turns her attention to what being a leader means, and how you can hire the best team members to represent your brand.

Anna lays down the key traits to look for in an employee, and how you can ask the right questions in interviews to uncover these. For her, it’s important to invest in the right people so your team can produce the best results.

What I liked most about this section was Anna’s breakdown of her daily routine. Insisting on the need to keep the pace moving, Anna shares a typical day in her life – from the time she wakes up to the time she goes to bed.

For me, this was a much more tactile way of understanding how a leader manages their time and activities. Even during non-working hours, Anna shows you how seemingly unrelated tasks can actually have a huge impact on your work life.

As well as this, Anna gives some attention to conducting meetings and making staff feel included. She places a lot of focus on how to maintain momentum and give valuable feedback to your staff.

Overall, this lesson offered good insight into how to build strong relationships with your team members so your business can flourish.

Inside Vogue: Leading with a Vision

Here, Wintour addresses some common hurdles you’ll likely encounter through your career. These include dealing with criticism, staying true to your vision, and handling rejection.

In this chapter, you also get to “sit in” on a post-show meeting filmed at Vogue. Anna gives you some background for understanding this meeting, and provides commentary over it to highlight key points.

She teaches you how to:

• Structure a meeting to ensure everyone is heard
• Understand the meaning of “run-throughs” in fashion
• Choose worthy collaborators for your projects
• Strike a balance between listening and decision-making

Editorial Decision-Making

As Anna advises at the beginning of this lesson, “always think about the big picture.” For Vogue, she says, it’s important to remind herself of what her brand stands for. This factors into every decision she makes as editor-in-chief.

In this section, you’re immersed in one of Vogue’s weekly editorial meetings. This meeting has Vogue’s values at its core as the staff discuss ideas for the new season. In particular, Anna leads the meeting into discussions of cultural relevance, and about who the Vogue reader is.

This chapter shows how you can foster productive discussions and ensure that your staff are all on the same page. The meeting is also a great example of Anna’s advice to “stay open,” as she listens to her team’s opinions and suggestions.

What I found interesting was that Anna was willing to share some of her failures as a leader and decision-maker. For instance, this includes the rushed and undignified 1993 cover and some tactlessness in maintaining political correctness.

At the same time, Anna also defends some of Vogue’s controversial choices and discusses the necessity of balancing risks. One example of this was the choice to feature Kim Kardashian and Kanye West on the magazine’s cover (a choice many thought was out of keeping with Vogue’s style).

Executing a Vision: Transforming the Met Gala

In this section, Anna teaches you:

• What the Met Gala is and her role in it
• How to collaborate with designers
• The significance of her work with the museum
• How to build relationships in your work
• The risks you should take as a leader

This lesson takes you through a brief history of The Metropolitan Museum of Art – mainly to highlight its relevance to Vogue’s brand. As she discusses, your job as a leader is to shake things up and push boundaries. For Anna, the Met Gala was a way to do this.

You’ll follow Anna through her meeting with her designer and gain insight into how Anna took a bold chance with a new business venture. She relates this to how she, as a leader, evolved Vogue as a brand and reinforced its relevance within its cultural moment.

Evolving a Brand: A Look Back at Iconic Vogue Covers

As someone who loves visuals, I found this section particularly fascinating. In it, Anna takes you through Vogue’s evolution throughout the years, and highlights some of the risks she made and relationships she built.

The key takeaway from this lesson was the need for a brand to be constantly changing and reflecting the culture it’s in. In fact, each Vogue cover she shows is supported by voice-over commentary, outlining the importance of this edition for growing the brand.

In this lesson, you’ll learn how to:

• Bring true value to the work you do
• Embrace change in your business
• Understand your audience’s wants
• Trust your collaborators and compromise
• Stay inspired and open to the new

Section 3/4: Working in Fashion

This topic delves into more fashion-specific aspects of leadership. In particular, this includes how to find your voice in the industry and collaborate effectively with photographers and models. Wintour also addresses her charitable work when it comes to spotting and lending a hand to aspiring designers.

Starting Out: Finding Your Voice and Succeeding

Addressing the responsibilities you’ll be given as a leader, Anna spends some time discussing how to interview potential employees. With her message of finding a great team ringing loud and clear, this is undoubtedly an important process that comes with its dos and don’ts.

With this in mind, this lesson teaches you how to do the following:

• Take action with your brand’s image in mind
• Develop taste when it comes to fashion
• Find and evolve your creative vision
• Learn new skills and gain experience

Much of this lesson is focused on how to start your career on the right foot and build a solid reputation for yourself as a creative leader. Anna shares some important tips on how to establish yourself as a confident and reputable boss, and how to push the boundaries to evolve your brand.

The Power of an Image: Photographers and Models

For Anna, images are crucial to Vogue. They communicate messages to their readers and carry with them their own narratives. Moreover, through images, you can make work that is thoughtful and meaningful.

In this section, Anna cements the importance of images by drawing attention to their cultural and political relevance. She also outlines the different types of photography at your disposal and takes you through the mutual relationship she has with photographers.

This lesson is mainly focused on how to build a good rapport with artists at the start of your career, and how to balance your vision by trusting your collaborators. Like most other lessons, Vogue is this section’s main case study, and Anna speaks specifically of what Vogue looks for in an image.

Designers: What It Takes to Succeed

In this lesson, Anna shares her advice for standing out in the industry. This includes how to confidently make bold choices and succeed in the field of fashion/design. Anna calls this the “shock of the new,” which has been pivotal for her career with the magazine.

Anna also teaches you how to:

• Use fashion to transport your readers
• Showcase your clothes in the best way
• Understand and use the “five-year plan”
• Succeed in business partnership

Spotting Designer Talent: CFDA/Vogue Fashion 

In my opinion, Anna’s discussion of the CFDA (Council of Fashion Designers of America) was one of the most memorable and enjoyable lessons of the whole course. Here, Wintour shares her mission to help aspiring designers after the tragedy of 9/11.

As Anna puts it, her aim with the CFDA was to create a “unifying spirit” across the nation, and to give the spotlight to emerging talent in America. While it might not be the most educational subject for the reader, it does act as a vital case study in how you can use your platform for change.

Anna outlines what the CFDA does and how it works through a committee and selection process. In fact, this serves to show the ways in which Anna took bold choices with her business to establish a new creative (and charitable) venture.

Case Studies: Lessons From Creative Leaders

In this section, Anna turns her attention to other creative leaders who have impacted her career. She also uses Vogue and Condé Nast to testify to the improvements she has made. 

Amongst her influences are Miuccia Prada and Michael Kors, whose advice she shares with her viewers. As a course dedicated mostly to Anna’s own take on her business, it was refreshing to hear some outside perspectives, even if they were views that she herself champions.

In sum, Anna teaches you how to:

• Understand your brand identity
• Channel your identity into your designs
• Know and love your customer
• Gain insight into your audience

Section 4/4: Parting Words

Leading with Impact

For Anna, it’s crucial for a leader to connect with their audience (and to find new and innovative ways of doing so). These are part of a leader’s responsibilities and should always be a priority.

Within this chapter, Anna relates her target audience and how they’re likely to have been affected by cultural and political events. Some examples she gives include the 2016 election, the Harvey Weinstein case, and the #MeToo movement.

As Anna states, you need to find the bigger meaning in your work and speak to a cultural moment. Vogue, she says, has a voice. And it’s a leader’s responsibility to ensure that voice is used.

For her, Vogue stands as a message of hope to its viewers and is largely devoted to meaningful causes. She recounts how Vogue adopted the new code of conduct for protecting models from harassment and raising much-needed funds during the AIDS crisis.

In fact, Anna stresses her sense of responsibility as a leader and the desire to give back to the community. She insists upon having a keen eye and ear for what’s going on in the world, and suggests a leader’s need to address it.

Along with this, Anna shares some parting words of advice – in particular, about being fearless, using your creative judgement, and learning by observing the world around you.

My Experience of Anna Wintour’s MasterClass

All in all, I found Anna’s MasterClass truly interesting. Every lesson comes with an end-of-video summary and the Workbook is very detailed. If you’re particularly interested in fashion and working for a magazine, this is likely to be a valuable course for you.

At the same time, I wasn’t sure if I’d enjoyed the course so much for its advice about leadership as for the compelling video content and behind-the-scenes look at the fashion world. It was also very example-heavy, and didn’t seem easily transferable as a result.

That being said, here are the pros and cons of this course to give you a better idea of whether this MasterClass is for you.

What I Liked About Anna Wintour’s MasterClass

Learn From an Important Fashion Figure

As Vogue’s editor-in-chief for over 30 years, Anna is an inspiring mentor for anyone looking to progress in the fashion world. A self-described creative leader, Anna takes you through how to solve problems, think inventively, and own your decisions.

In her MasterClass, Anna’s advice is fashion-focused but, at the same time, applicable to many career paths. She shares a lot of advice about how to manage and motivate your team and cement your position as a leader and decision-maker.

If you’re keen on developing your leadership skills, Anna Wintour is an unquestionable role model who has a proven track record of succeeding in business.

Strong Visual Examples Throughout

If you’re a visual learner, Anna Wintour’s MasterClass is ideal for you. Every lesson includes strong visual examples to support Anna’s points and illustrate the choices she made with her brand. These serve as case studies for Anna’s lessons and give a physical demonstration of what Anna hoped to achieve.

Mostly, this includes iconic (and not-so-iconic) Vogue covers throughout the years, and examples of shoots that hit or missed the mark when it came to conveying the magazine’s vision. As a largely visual industry, this image-heavy approach suited both the video format and the wider world Anna spoke to.

Ample Visual Demonstrations

Similarly, Anna’s MasterClass is replete with physical demonstrations of each topic. This includes footage of:

• Weekly editorial meetings
• Post-show seminars
• Run-throughs
• Consultations with designers
• Interviews with collaborators
• Preparation for the Met Gala

In these examples, you get to be a fly on the wall in Vogue’s headquarters, as well as behind the scenes at the Metropolitan Museum of Art and the CFDA. Aside from being visually fascinating, these demonstrations serve to show you Anna’s leadership in action.

She shows you how she communicates with her staff and strikes a balance between listening and making decisions. It was interesting to see how Anna would lend the floor to her younger employees to ensure everyone’s voice was heard.

For me, this was a fantastic opportunity to see a creative leader succeeding in her business environment. It also shows how, as a leader, you can guide discussions towards a productive end.

Helpful End-of-Lesson Summaries

One feature of this MasterClass that stood out to me was the end-of-lesson summaries. These are quick bulletin-style notes that sum up the lesson’s main points. If you’re an avid note-taker, this is an effective way to summarize each chapter and give a brief overview of Anna’s tips.

An Interesting Look into the Fashion World

As I mentioned, Anna’s generous visual demonstrations are not only educational, but also offer a compelling and exclusive look into the fashion world. You get to sit in on Anna’s guest-list prep for the Met Gala and even watch her team plan the next edition of Vogue.

While I don’t think this MasterClass only has merit for those in the fashion industry, it is particularly insightful for those who are truly passionate about the field. In the “Working in Fashion” section, in particular, much of Anna’s leadership advice is geared towards collaborating with designers and photographers.

If you’re in the field of fashion (or working towards it), this MasterClass is likely to hold even more value and interest for you.

What Could Be Improved

Little Focus on Fashion Education

Despite Anna’s focus on growing up during the cultural revolution of the 1960s in London, she gives little attention to her education in fashion, or how you can use your schooling to progress into a career.

Instead, she dives almost immediately into her first editing job. As interesting as this is, it doesn’t seem helpful to those with little to no experience, or for those coming into fashion from a different field entirely.

I would’ve liked to have seen Anna address this issue more, particularly as fashion school has become increasingly popular in recent years. In fact, she could’ve better addressed the skills employees are looking for when they first hire new talent, and what your resume could include to reflect this.

Controversial Business Reputation

As I discovered when researching this MasterClass on Reddit and similar forums, I found that Anna Wintour had a controversial business reputation. In the media, she’s commonly hailed as “Nuclear Wintour” and known for her feisty personality and even bullying of younger staff.

I can’t say I witnessed this in the sit-ins from the class, but it goes without saying that the course is designed to show Anna in the best light. While it didn’t ruin my experience of the course, knowing about her reputation did make me question the validity of some of her advice.

It’s definitely worth taking this MasterClass with its subjective nature in mind, and use your own judgement when evaluating Anna’s advice.

Heavily Subjective

As I touched on earlier, this course is undoubtedly subjective in that it offers one leader’s advice on how to run a business. In fact, Anna has often been criticized for her leadership style, and it’s worth remembering that her point of view is just one among many.

Learn by Example

On the one hand, this is a definite benefit of the course – you get to see how Anna works to create successes like the CFDA and the Met Gala. At the same time, some of these examples seem too distant for the everyday viewer, who’s probably far-removed from the glitz and glam Anna sees every day.

Because of this, I would’ve liked Anna to have spent more time discussing the day-to-day leadership skills you can use in your own career, like she briefly did with her “daily routine” segment. I think that a better balance between theory and practice would’ve made the class more relatable to a wider range of viewers.

Who Is the Course For?

Overall, I’d say this course is more geared towards young professionals that are working their way up in the fashion industry. On a scale of 1-10 (1 being a beginner and 10 being a seasoned professional), this MasterClass is best suited to those at 5 or higher.

While Anna does frequently address young people in particular, it’s always with an assumed role in leadership already. In fact, this MasterClass is more about how to be an effective leader rather than how to become one from a lower position.

In sum, Anna teaches you how to work for yourself – not someone else – and how to work with your own brand vision in mind.

Learn how to:

• Plan and execute a creative vision
• Understand and evolve your brand
• Find your voice and succeed
• Navigate the world of fashion
• Lead creatively and with impact

How Much Does the Course Cost?

At the time of writing MasterClass had three subscription offers. The cost of these (per month) is:

• Individual (1 user) $15
• Duo (2 users) $20
• Family (6 users) $23

All are billed annually, which at first glance may seem pricey. 

However, you can considerably reduce your costs by taking as many courses as possible.

With over 150 courses on the platform you’re likely to find quite a few to interest you. Even if you buy an individual membership and find only 10% of the courses of interest this still works out to only $12 a course:

$180 (annual individual membership fee) / 15 courses = $12.

And if you join with friends or family then the cost of each course is drastically reduced. Check out our MasterClass review or MasterClass cost articles to see how.

Bearing in mind that these classes are taught by global leaders in their fields the value is unbeatable. You can pay over $100 for an online course taught by someone you’ve never even heard of, never mind the caliber of teachers on MasterClass.

What’s more, MasterClass also offers a 30 day refund if you’re unhappy with your purchase.

You can also purchase MasterClass as a gift.

Alternatives to Anna Wintour’s MasterClass

On MasterClass, there are other business/leadership courses available:

• Tan France – Fashion
• Kris Jenner – Personal branding
• Bill Clinton – Inclusive Leadership
• George Bush – Authentic Leadership
• RuPaul – Self-Expression and Authenticity
• Dr Jane Goodall – Conservation
• Sara Blakely – Self-Made Entrepreneurship
• Richard Branson – Disruptive Entrepreneurship
• Chris Voss – The Art of Negotiation
• Daniel Pink – The Science of Sales and Persuasion
• Doris Kearns Goodwin – U.S. Presidential History and Leadership
• Bob Iger – Business Strategy and Leadership
• Paul Krugman – Economics and Society
• Bob Woodward – Investigative Journalism
• Howard Schultz – Business Leadership

Outside of MasterClass, there are other options for both business and fashion courses. On FutureLearn, there’s a class dedicated to Fashion and Business. There’s also a similar course on Coursera.

That being said, I don’t think these courses can compare to the level of teaching and high production values you get with MasterClass. Aside from learning directly from experts in their field, you also have the benefit of having all class content in one easy-to-navigate place.

You could also consider photography classes like Jimmy Chin’s or Annie Leibovitz or check out our review of best online fashion courses.

Anna Wintour MasterClass: What Others Have Said

From my research into this MasterClass, I found some mixed reviews. On the positive side, one student was impressed with the quality of teaching Anna gave, and found great value in the course as a whole.

“I am deeply inspired by her examples and her views on leadership. One of the strengths that Anna has taught me is tenacity and courage. I believe it’s one of the most important traits ever and a priceless attribute. It’s a must-have for every man and woman regardless of race, language or religion.”
- Comment from the community

Others also agreed that her course was inspirational and practically helpful, even if they weren’t in the field of fashion themselves.

“I am not in the fashion industry. I wanted to hear and understand what it’s like to work in the fashion industry. I loved listening to Anna Wintour. She is knowledgeable, beautiful, and funny.”
- Comment from the community

“Fascinating. A great mentor for business people in the creative industry. At times a little repetitive, but still interesting.”
- Comment from the community

With this in mind, there was also less glowing feedback, particularly from those who felt that the course was lackluster and sub-par compared to other courses.

“I expected more from this class to be honest. More detailed insight. It was still a good course but I learnt the most out of the course with Chris Hadfield.”
- Comment from the community

Some even criticized her suitability to teaching a MasterClass, especially with her reputation for being a difficult and even intimidating manager.

“Leadership is not about bravado, mystique and fear - which quite publicly is how Anna Wintour has run Vogue. Whilst you can’t argue with the results, the way in which she treats her staff is atrocious; i.e. not allowing junior members of the team to speak with her, staff so scared they don’t want to take the elevator with her. The novel aside, there has been plenty of articles on ‘Nuclear Wintour’ and it’s a poor choice of instructor for MasterClass.”
- Comment from the community

In fact, Anna Wintour has undoubtedly been a controversial figure in the limelight and it’s understandable that a class from her is unlikely to appeal to everyone. All in all, there seemed to be a clear divide in opinions, with some enjoying the course and others feeling it lacked insight.

For most, the glimpse into the world of creative leadership as it appears in the Vogue headquarters was fascinating to many. Regardless of her controversy, Anna has clearly moved Vogue forwards throughout the years and left her mark on the fashion industry. Many students found this inspiring and enjoyed Anna’s professional advice.

Verdict: Is The Anna Wintour MasterClass It Worth It?

To me, the Anna Wintour MasterClass is an interesting look at how a creative leader can transform and elevate a brand throughout the years. I found the confidence and conviction inspiring, particularly as a female leader who navigated her fair share of sexism in the industry.

Most students who took the course considered it a worthwhile investment and praised MasterClass for its accessible content. At the same time, her lessons were mostly case studies and I felt they lacked value when it came to delivering universal advice.

If you’re seriously interested in fashion and/or creative leadership, this course is definitely worth the watch. But it’s worth bearing in mind that much of the content involves following Anna’s personal career journey and running through several case studies.

I do think Anna’s MasterClass has great merit, especially for young women hoping to progress in a leadership role. Her parting words, in particular, are full of motivation and encouragement for her viewers.

Learn how to:

• Plan and execute a creative vision
• Understand and evolve your brand
• Find your voice and succeed
• Navigate the world of fashion
• Lead creatively and with impact

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