Anna Wintour MasterClass Review: Is it Worth it?

Anna Wintour MasterClass review synopsis

What you’ll learn: Learn the foundations of Anna Wintour’s success in her career. The course includes tips on creativity and leadership through the lens of her experience in the worlds of journalism and fashion.

Course Length: 12 lessons, approximately 142 minutes long or a little less than 2.5 hours.

Similar courses: Es Devlin: Turning Ideas into Art, Bob Iger: Business Strategy and Leadership, Parris Goebel: Creativity in Choreography, Chris Voss: The Art of Negotiation, Jeff Goodby and Rich Silverstein: Advertising and Creativity, Tan France: Creating your own Style

Do I recommend Anna Wintour’s MasterClass? Yes. The lessons in Anna Wintour’s MasterClass are more high-level or aspirational than some others on the platform. But the short length and the detailed case studies make the class worth taking.

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I’m always interested in the stories of powerful women. I seek out those from women who’ve led big businesses or projects and have found new ways to chip away at the glass ceiling.

Anna Wintour, while a controversial business leader, is no doubt a powerful woman. She’s a British-American journalist who’s served as editor-in-chief of Vogue since 1988 and Global Chief Content Officer for Condé Nast since 2020.

I was skeptical of this course at first because of the controversy around her leadership style — she was the inspiration for Merryl Streep’s character in the popular movie The Devil Wears Prada, after all.

But her insights into how to lead and manage creative projects surprised me, and I found myself inspired by how she’d overcome challenges as she discovered her place at Condé Nast.

“As you move along in your career, it’s important to remember that opportunities come in the most unexpected ways.”

Lesson 6, Executing a Vision: Transforming the Met Gala

In this review, I’ll take a deep dive into exactly what the Anna Wintour MasterClass offers, including its cost, curriculum, and whether or not it’s worth it for you.

Disclosure: In the interest of full transparency, Codeless uses affiliate links in our MasterClass reviews to cover our site’s costs.

Our Verdict

I would recommend Anna Wintour’s MasterClass, especially if you’re going into it wanting high-level advice. There is enough insight into Wintour’s career for aspiring professionals to walk away inspired.

Anna Wintour MasterClass Increase your creativity and leadership skills.

$15 /month
  • You get to learn from one of the most important icons in the fashion world
  • You get to see high profile Vogue meetings in actionvariation of clips and sceneryin genius, unconventional way
  • There are strong visuals throughout the whole course
  • The workbook includes helpful summaries
  • She talks too fast for the 2x speed if that’s how you like to watch these classes
  • The course workbook doesn’t really contribute to the class

A few frequently asked questions (FAQs)

Let’s answer some questions about the Anna Wintour MasterClass.

Do I need a subscription to access this course?

Yes, in order to access Anna Wintour’s MasterClass, you need to subscribe to the MasterClass platform.

By subscribing, you’ll get access to the 180+ courses MasterClass offers in several categories, ranging from cooking, baking, photography, interior design, music, dancing, writing, poker, makeup, and even negotiation.

What is Anna Wintour’s Net Worth?

Anna Wintour doesn’t specifically discuss her net worth in her MasterClass, but it’s reported to be around $50 million. She’s paid an annual salary of $2 million for being Vogue’s editor-in-chief.

How long is the MasterClass?

Anna Wintour’s MasterClass contains 12 lessons, clocking in at a total of 142 minutes or a little less than 2.5 hours.

Does MasterClass have a cancellation policy?

Yep, you can cancel your subscription whenever you’d like. There’s also a 30-day money-back guarantee if you’re unhappy with your purchase.

Is the Anna Wintour MasterClass worth it?

Yes. Despite the media mogul’s controversial management style, her advice on how to tackle creative projects and get promoted is inspiring for those looking for a career in fashion or media.

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About Anna Wintour

Anna Wintour is a business leader with a controversial reputation. She’s editor-in-chief of American Vogue and the chief content officer of Condé Nast. She is widely accepted as the most influential figure in the fashion world.

Anna Wintour is at the helm of American Vogue, which reaches over 12 million readers in print and an average of 1.2 million monthly visitors online.

During her 25-year tenure at American Vogue, Wintour has made her mark by featuring celebrities on the cover and taking Vogue’s fashion pages away from the studio lights and to the public streets. She is now using Condé Nast’s flagship title to champion new American designers through the CFDA and Vogue Fashion Fund.

How much does Anna Wintour MasterClass cost?

Anna Wintour’s MasterClass isn’t available as a single purchase. To access the course, you’ll have to subscribe to the MasterClass online learning platform. Remember, you’ll also be getting access to other quality courses from well-known names such as Bobbi Brown, Kelly Wearstler, and Christina Aguilera.

You can do so through three payment plans: Standard, Plus, and Premium.

anna wintour masterclass cost pricing
Anna Wintour MasterClass Cost

MasterClass’s Standard Plan is $15 per month, billed annually. You can watch lessons from any MasterClass, using one device at a time, as well as download each class’s workbook and interact with their community forums.

The next-level Plus Plan costs $20 per month, billed annually. It includes everything the Standard Plan includes, but it also allows you to access MasterClasses on two devices at the same time. You can also download lessons for offline viewing on iOS devices.

The Premium Plan costs $23 per month, billed annually. It includes everything in the Plus Plan, as well as access to MasterClass content through six devices.

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What is included in the Anna Wintour masterclass?

Runtime: 142 minutes, or a little less than 2.5 hours

Course Value: 4/5

Lessons:  12 video lessons

Supplementary materials:  A PDF workbook and community hub for students

Supplementary workbook

When you start a MasterClass, you don’t just get the video lessons. You’ll also receive a downloadable workbook to accompany the course.

Anna Wintour’s workbook summarizes the main takeaways from the course lessons and includes recommendations for additional reading.

This workbook is great as a follow-along guide to the course, and it’s also a great solution for people who prefer to read rather than watch or listen. The workbook captures a lot of the lessons taught in the videos.

The MasterClass Hub

Along with a workbook, MasterClass courses also include access to a community hub where students can interact with one another to discuss course content and ask each other questions.

Anna Wintour’s community hub has topics on things like how to run creative meetings, how others have dealt with career failures, how to not let people tell you ‘no,’ and more.

anna wintour masterclass community hub
Anna Wintour MasterClass Community Hub

Here’s a snapshot of an example forum question where students talk about creative leaders that they would turn to for advice in their current careers if they could:

anna wintour masterclass community hub sample
Anna Wintour MasterClass Community Hub Sample

A complete breakdown of the Anna Wintour MasterClass curriculum

As a student in Anna Wintour’s MasterClass, you should expect lessons on how to land a job in media or the fashion industry and tips on how to develop your creative eye. You’ll also learn how to reflect culture, and world events in your own creative work.


  1. Introduction
  2. Getting the Work Done: Anna’s Management Tips
  3. Starting Out: Finding Your Voice and Succeeding
  4. Inside Vogue: Leading With a Vision
  5. Editorial Decision-Making
  6. Executing a Vision: Transforming the Met Gala
  7. The Power of an Image: Photographers and Models
  8. Evolving a Brand: A Look Back at Iconic Vogue Covers
  9. Designers: What It Takes to Succeed
  10. Spotting Designer Talent: CFDA/Vogue Fashion Fund
  11. Case Studies: Lessons From Creative Leaders
  12. Leading With Impact
anna wintour masterclass curriculum

Course summary:

Anna Wintour is succinct in her MasterClass lessons and clearly comfortable talking in front of the camera. Throughout her MasterClass, you get to see footage of her actually working on cornerstone events, like the Met Gala, and she talks through how she was able to bring them to life.

One of the cool things about Anna Wintour’s MasterClass is that it’s more than just clips of Wintour lecturing students. It also includes documentary-style snippets of her working on real projects and selections from media interviews.

The course kicks off with an introduction to Wintour as the instructor, including a brief summary of her time at Vogue and Condé Nast.

anna wintour masterclass course introduction
Anna Wintour MasterClass Course Introduction

Then, Wintour dives into her management style, including tips on managing a team, how she gives feedback, and what she expects from candidates during the interview process.

anna wintour masterclass office tour
Anna Wintour MasterClass Office Tour

Walking students through the offices at Vogue, Wintour discusses how to lead with a vision and how she encourages creativity and collaboration amongst her team.

These lessons include summaries of some of the most forward-thinking editorial choices she’s made or managed throughout her career and how she handled some of her most controversial decisions.

anna wintour masterclass met gala
Anna Wintour MasterClass Met Gala

As a case study, Wintour talks about how she helped make the famous Metropolitan Museum of Art (Met) Gala in New York the cultural and fashion event that it is today.

After discussing the event as a whole, she takes a deep dive into topics like how to think about photography, design, and other visual elements in fashion media.

anna wintour masterclass vogue covers
Anna Wintour MasterClass Vogue Covers

Wintour then discusses some of the most controversial covers of Vogue magazine throughout her career and how she worked with some of the world’s most renowned designers to make them happen.

To wrap up her course, Wintour covers some of the most important designers in the fashion industry before ending with insight into how iconic leaders execute their jobs day-to-day.

What I learned

I don’t work in the fashion industry, and it’s not really a personal goal of mine. Even so, I found a lot of value in this course, and there’s even more value for people targeting a career within fashion.

While most of my takeaways from this course could be categorized as high-level advice, there were a few actionable takeaways that also made this class worth the short time it took to watch.

4 takeaways from this MasterClass

1. You have to learn about the team you’re working with before you change their mind about something.

Listening to Anna talk about how she transformed the Met Gala was incredibly valuable because she spoke in-depth about the team. She covered how she needed to get to know those who worked for such a traditional institution before changing their minds to get them on board with her out-of-the-box vision.

2. Interviewers want to know how you think more than what you’ve done.

I thought it was interesting that Wintour insisted she didn’t care what people were wearing in interviews. And even more than their previous experience, she wanted to know what they read, what they found interesting about the world, and what they were passionate about. In future interviews, I’ll focus a little bit more on who I am instead of what I have done in my past.

3. Learn from observing the world around you.

Wintour puts a lot of emphasis on observing “the moment” that the world is in and how you can reflect that “moment” in your work. For example, Anna focused on how fashion was a reflection of the mood of the 60s.

anna wintour masterclass takeaways

4. Take criticism and move on.

Sometimes creative people dwell on criticism. Her advice is to not dwell too long — take it, listen to it, digest it, spit it out if you have to, and move on. It’s much easier said than done, but you can’t take criticism too personally. It’s criticism of your work, not of you. Learn to separate the two.

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Memorable quotes from this MasterClass

“I was thrown into my career frankly with ignorance. You had to learn everything you had to do. You had to know how to multitask. I think it also gives you a certain strength that you’re not stuck in one box.”

Lesson 1, Introduction

“When you are interviewing for a job. First of all, always tell the truth, second, don’t say I love the theatre because you happen to know whoever is interviewing you loves the theatre. Unless you really do and can give a real example.”

Lesson 3, Starting Out: Finding Your Voice and Succeeding

“I think that there are so many ways to tap into creativity. Particularly in today’s world when information is so readily available. There are many ways to grow one’s eye and expand one’s creative vision. Don’t spend all your time glued to your phone or computer. There’s nothing more rewarding than seeing things in person.”

Lesson 3, Starting Out: Finding Your Voice and Succeeding

“The Met Gala was not always the culture and fashion event that it is today. It took many, many years to transform it.”

Lesson 6, Executing a Vision: Transforming the Met Gala

“As you move along in your career, it’s important to remember that opportunities come in the most unexpected ways.”

Lesson 6, Executing a Vision: Transforming the Met Gala

Anna Wintour Masterclass pros and cons

If you’re still not sure whether or not the Anna Wintour MasterClass is for you, here’s a breakdown of the pros and cons you should consider.


  • You get to learn from one of the most important icons in the fashion world
  • You get to see high profile Vogue meetings in action
  • There are strong visuals throughout the whole course
  • The workbook includes helpful summaries


  • There’s not a lot of in-depth fashion education
  • Wintour has a controversial business reputation

Do I recommend this Masterclass?

Yes, I would recommend Anna Wintour’s MasterClass, especially if you’re going into it wanting high-level advice.

In my opinion, the fact that it only takes 2.5 hours to watch the whole thing makes it worthwhile all by itself, and there is enough insight into Wintour’s career for aspiring professionals to walk away inspired.

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