Anna Wintour’s Masterclass Review

Are you a fan of celebrated Vogue editor-in-chief, Anna Wintour? Curious as to whether her masterclass on creativity and leadership is worth your time? Then we welcome you to our very own Anna Wintour’s Masterclass Review!


Course Structure

The course consists of twelve “chapters” that are videos of about 15-30 minutes in length discussing different topics. There is one workbook which covers the entire course (summarising each lesson with additional information and resources). There are also smaller pdfs. available for specific lessons that outline the important points in writing, which makes it easier to review the most salient information.

Course Content

The videos are of a very high production value. It really was a pleasure to sit back and listen to Anna’s advice, observations, and what being an effective leader means to her.

On the other hand, a lot of her advice felt a bit trite and commonsensical. For example, “don’t micromanage,” “not everyone is going to agree with you,” and “make mistakes and learn from them.”

We are taken to some of her editorial meetings with her Vogue team. She sits with her arms crossed and sunglasses on as the various editors pitch ideas to her. It was not as glamorous as one would expect. Some of the editorial staff looked sleep-deprived, with uncombed greasy hair and an overall sloppy appearance. Did they not know they would be filmed that day? A stark contrast to a similar scene in “The Devil wears Prada.”

A lot of the material is aimed at editors, designers, and photographers. This seems to limit the scope of the course, in our opinion. Anna’s editorial decisions regarding Vogue covers is discussed in detail – her first cover ( Vogue, November 1988. Michaela Bercu photographed by Peter Lindbergh) featured an Israeli model wearing jeans and not looking directly at the camera.

For that particular moment in time, this was a strong departure for Vogue – until then, Vogue had always featured close-ups of models, looking straight at the camera and only wearing couture (Vogue, August 1986. Cindy Crawford photographed by Richard Avedon.)

You are leading. You are not following.

Anna Wintour

Main Points

The main takeaway from the course is that you should be fearless. As a leader, you need to have the courage of your convictions, and not be too influenced by the opinions of others around you. On the other hand, you need to surround yourself with talented people you respect, and accept their feedback without micromanaging.

The rest of the course gives a behind-the-scenes look at the organization for the Costume Institute annual Gala, the CFDA Fashion fund, what criteria the panel is looking for in their selection of new designers, and case studies of successful figures such as Christopher Bailey and Miuccia Prada.


Anna concludes by getting a bit political, she states: โ€œI think about how we can use Vogue as a platform for change, a platform for activism, a platform, very importantly, for the fashion industry.โ€ In short, she urges viewers to take their leadership position seriously, to support others in their industry, and to find ways to give back.

Engage with whatever is happening in the world in a thoughtful way, and stand up for what you believe is right. Take a point of view, and be thoughtful about it, and stand by your convictions.

Anna Wintour


Did we enjoy Anna Wintour’s Masterclass? Sure!

Did we think the price was justifiable? Not really.

With the Masterclass model, it makes little sense to purchase one course only. It is much more cost-effective to purchase the all-access one year pass. (If you think you are interested in their other courses.) Their platform is great and we are looking forward to following along their other courses from Diane von Furstenberg, Marc Jacobs, Sarah Blakely, and Misty Copeland. If, on the other hand, you are ONLY interested in purchasing the Anna Wintour course we cannot say we think it’s worth the price.

“Why,” you ask? Mainly because a lot of this information can be found for free online. Sure, it’s not as pretty and organized as it is in the masterclass, but we did not think any of the information was groundbreaking. In fact, the 2009 documentary “The September Issue” gives you a great behind-the-scenes look into what goes on at Vogue, in preparation of the most important issue of the year.

In addition, Youtube is full of in-depth interviews of Anna. The video below of her address at Oxford University is full of good advice (some of it identical to what she shares in the course.)

Anna Wintour’s address to the Oxford University Union

You can also check out this little gem we just found. A BBC documentary from 2000 entitled “Boss Women: Anna Wintour” ( the quality is not too good but it’s worth a look!) As a bonus, it features a young Plum Sykes (author of Bergdorf Blondes), who is still a contributing editor for the magazine today.

Boss Women: Anna Wintour (2000)

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  1. Definitely going to check out those interviews, that’s the best way to get a better read on people (as you know). I appreciate the consistency in her business philosophy in interviews and masterclass, but I also appreciate that you spent the money to share that insight with us. ๐Ÿ˜‰๐Ÿ˜Š

      1. Well since you asked!!! ๐Ÿ˜ฌ I think Gordon Ramsay was just added to the roster! But I know it’s not related to the blog ๐Ÿ™ˆ๐Ÿ™ˆ๐Ÿ™ˆ๐Ÿ™ˆ๐Ÿ™ˆ

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