Anna Wintour MasterClass Review: Worth it?

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When I say struggling artist, what do you imagine? Someone holding a paintbrush, staring intently at a blank page, and living in an attic somewhere? Check, check, and check. The struggling artist in the attic (it has got a nice ring to it) is me. My art is fashion. It is the new frontier of creative expression.

While paintbrushes and sketchpads hold a certain romantic, old-school charm, modern fashion has evolved to be all about mood boards and Adobe Illustrator sketches. That has become the world of high fashion. It is a world that is all about creativity and breaking the norms where a single runway show has the power to set global trends.

When I was young, kids my age read storybooks, but I grew up reading Vogue. Vogue has been like the Bible and everything Holy to me ever since I could differentiate between chiffon and chambray. I have devoured every page of it and meticulously clipped out everything from ethereal runway looks (Iris van Herpen Fall 2022 Couture looks come to mind) to street-style inspiration (who can say no to Hailey Beiber and boyfriend blazers).

My dorm room walls now resemble a fashion mood board crime scene – a chaotic symphony of sequins, semi-draped silhouettes, and handcrafted headpieces that could make even Lady Gaga jealous.

All that is well and good, but there is one (not so tiny) hitch: my design skills need a lot of work. Currently, my designs are stuck between a toddler wielding finger paints and a creative black hole. Sure, I can distinguish a peplum from a plunging neckline, but translating those skills into wearable (and hopefully stylish) pieces felt like a fashion faux pas waiting to happen.

Stuck in this constant loop, I needed some inspiration to help me get out of it. That is when God finally answered my prayers in the form of Anna Wintour’s MasterClass.

Yes, you read that right. I am talking about THAT Anna Wintour, who is known for her icy persona and signature bob. Her class on creativity and leadership immediately piqued my curiosity.

Fashion is a story – a narrative woven through fabric, color, and silhouette. In this review, I will dissect the content, structure, key takeaways, and whether Anna Wintour’s wisdom finally turned this Vogue-obsessed student into a budding fashion icon (I can always dream, right?).

So, grab your sketchpads and let your inner trendsetter free.

Anna Wintour MasterClass Review Summary:

In case you’re pressed for time, here’s a brief summary for your convenience.

You’ll learn how to:

  • Understand the concept of creative vision
  • Execute ideas that revolutionize fashion
  • Elevate your personal style 
  • Grow your business through marketing and branding
  • Lead large teams smoothly

Time Duration 

This class is 2 hours and 36 minutes long.


  • Learn from a fashion pioneer
  • Get an inside look into Vogue’s brainstorming process
  • Exceptional production quality
  • End of lesson summary that helps with information retention
  • Engaging and versatile content structure


  • It does not focus on fashion advice
  • Business advice is not relatable for everyone

Alternatives to Anna Wintour’s MasterClass

If you want to pursue creative fields, you may enjoy Es Devlin Turning Ideas Into Art, Devon Rodriguez Draw And Paint Realistic Portraits, and Jeff Koons Teaches Art and Creativity.

Suppose you are more focused on the leadership aspect. In that case, you will like Indra Nooyi Leading With Purpose, Bob Iger Teaches Business Strategy and Leadership, and George W. Bush Teaches Authentic Leadership.


Anna Wintour’s MasterClass is different from your average fashion course. It covers topics beyond sketching techniques and delves into the business of fashion, building a brand, and leading a creative team. With insights into her approach to trends and the ever-changing media landscape, this class is a must-watch for aspiring designers and fashion enthusiasts.

Anna Wintour MasterClass Review

Who is Anna Wintour?

Anna Wintour is a fashion industry icon with her trademark power suits, bobbed haircut, and steeling gaze that could melt glaciers. She is a legend, someone who has redefined the role of editor-in-chief and transformed  Vogue magazine into a cultural powerhouse.

A woman of her stature indeed has tons of awards to back up her talent and skills. Her influence on the fashion industry is paramount. She has been awarded the prestigious Dame Commander of the Order of the British Empire (DBE) for her services to British journalism and fashion. She has singlehandedly made Vogue a synonym for high fashion.

Most people know Wintour but don’t know that she took control of Vogue in 1988 and has completely revolutionized the fashion industry since then. She firmly believes that fashion is not about reality, and her work reflects her philosophy.  She created a magazine that depicts a more aspirational and glamorous (kind of unattainable) side of the industry.

She put a ban on boring society portraits. She made Vogue a platform for cutting-edge designers (remember Proenza Schouler?), groundbreaking photography (Jvdas Berra’s ethereal), and a celebration of outspoken celebrity style.

Despite her cold exterior, Anna has always supported young designers like Alexander McQueen and helped them rise to international recognition. She has transformed Vogue from “just a fashion magazine” to a cultural trendsetter, influencing everything from runway looks to street style.

Wintour is not only the creative mind behind Vogue’s success but also the shrewd businesswoman who understands the power of branding. Her sharp eye for talent and her unwavering commitment to quality have made Vogue a must-read for fashion enthusiasts and industry insiders alike. That is why you will see framed Vogue covers at many celebrity households. Vogue magazine covers are sometimes pieces of art.

For over three decades, Anna Wintour has led Vogue with a singular focus on excellence. She is a demanding leader, known for her meticulous attention to detail and her ability to spot trends before they even emerge. She is unafraid to take risks and push boundaries, constantly innovating and keeping Vogue at the forefront of the fashion world.

So, why does a fashion figure like Wintour have the authority to lead a MasterClass on creativity and leadership?

Because she is the living embodiment of both. Her vision has shaped the fashion landscape for over a generation, and her leadership style has transformed Vogue into a global phenomenon. With her unparalleled experience and a keen eye for talent, Anna Wintour is the perfect guide to embark on this journey of creative exploration and leadership mastery.

Who Should Get Anna Wintour MasterClass? 

Anna Wintour’s MasterClass is not for everyone looking to understand creative leadership. But if you crave a front-row seat to the world of fashion and beyond, there’s a good chance you’ll find something inspiring here. There are a few people who can benefit the most from this class:

Aspiring Fashionistas: If you dream of transforming your tissue paper sketches into runway showstoppers, Wintour will explain her creativity. She will help you develop your unique aesthetic style and translate simple ideas into captivating designs. She also teaches how to navigate the fashion industry, identify trends, and create a brand that stands out from the crowd.

Creative Leaders in All Fields: Leadership is a vast concept and is not confined to the norms of the fashion industry. Wintour’s course offers insights for anyone in a leadership role. She focuses on building strong team, encouraging innovation, and maintaining a clear vision; these things are applicable across all industries (from tech startups to NGOs) 

Entrepreneurs with a Vision: Wintour’s journey with Vogue started three decades back. Since then, she has worked to build a brand. She will teach you her strategies for brand development, navigating a competitive market, and leveraging new media to expand your reach. Any entrepreneur in the making will learn essential lessons from this class.

Fashion Enthusiasts Seeking Insights: Fashion is an exclusive industry, and few people understand its inner workings. However, Wintour’s course offers a glimpse into the editorial process, the collaborative process between designers and editors, and the ever-evolving landscape of fashion.

Those Seeking Inspiration and Confidence:  Sometimes, all it takes is a spark to ignite your creative fire. Anna Wintour’s MasterClass is a wellspring of inspiration. Her steady focus, dedication to excellence, and ability to navigate challenges will motivate anyone to pursue their creative dreams with passion and perseverance.

If you are inspired by creativity and want to learn from top experts in their fields, then MasterClass has amazing courses for you to take. Here’s a list of Best MasterClass for you. Ultimately, Anna Wintour’s MasterClass can benefit anyone who desires to push boundaries, cultivate a strong creative vision, and confidently lead. 

What does Anna Wintour’s MasterClass cover?

Phil Ivey’s MasterClass teaching poker is 2 hours and 36 minutes long. It is divided into 12 video lessons of 10-15 minutes each. She takes you through her journalism journey and gives you a peek behind Vogue’s guarded curtain.

The world knows Wintour to be this ice queen of a person with no empathy, but you get to explore a different side of her. She has supported and uplifted young designers like John Galliano, Tom Brown, and even Marc Jacobs. These designers owe their careers to her, and you get a chance to learn from such a powerful global influencer. 

Anna’s course includes a supplementary 35-page workbook summarizing the video lessons. This is perfect for people who prefer reading to understand complex concepts. The workbook also recommends additional resource material that can help you build a career in fashion.

Anna Wintour’s community hub provides valuable insights on conducting creative meetings, addressing career setbacks, and overcoming rejection. MasterClass offers a dynamic community platform that connects individuals with similar interests. It acts as an invaluable space for sharing experiences and receiving support from like-minded individuals with similar aspirations.

MasterClass as a learning platform is quite affordable. The yearly subscription costs $120, and if you take only 12 classes per year, it is still just $10 per class. Here’s a complete breakdown of MasterClass Pricing so you can make an informed decision. 

The lesson plan is as follows:

  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

Summarizing Anna Wintour’s Video Lessons

Anna Wintour introduces herself and acknowledges many people are curious about who she is, how she approaches her work, and what she believes. She talks about her childhood and her parents. She grew up in London with her parents, who were both journalists, and that is where her interest in journalism started budding.

Wintour emphasizes the importance of building a solid team. She says that you are nothing and no one without your team. She walks you through the management techniques—including how to develop and manage a team and how to give feedback—that has helped her be an effective leader.

In her life, Anna has conducted thousands of interviews and developed a keen sense of recognizing talent from miles away. She gives pointers on what to do during an interview to stand out, like being honest about your likes, being on time, and always being prepared.

Then she discusses what not to do during an interview, like not pretending you are somebody you are not or being unclear with your replies. She also shares practical tips for those starting out in their careers, including how to discover your creative voice and the best ways to interact with your mentors.

In this rare chance, Anna invites you (virtually) to her office at Vogue. She shows how she leads with a clear vision and point of view while encouraging creativity and collaboration among her team members. Anna also addresses how she deals with criticism.

Anna explains that criticism is often regarded as taboo, but you can learn a lot from it. At the same time, you have to remain true to your vision, particularly in media and journalism. It is even more critical for one’s audience, whoever you are addressing or talking to, to understand what you are standing for and realize that this is the core of who you are. 

Being afraid of failure makes you a coward and is not a sign of a visionary. Anna’s forward-thinking and sometimes surprising editorial choices have kept Vogue relevant for more than 30 years. She explores the process behind several of her controversial covers and features and explains why making mistakes is vital.

Any aspiring fashion enthusiast knows the significance of the MET Gala, but you might not know that it was not always the cultural touchstone it is today. Anna brings you behind the scenes of the 2019 Met Gala. She shows how attention to every detail makes the gala one of the year’s most influential and talked-about events.

Photography is critical for communicating your message and your brand. Anna discusses the impactful cultural movements in Vogue Magazine’s history and the photographers and models involved in those shoots. 

Anna recalls the masters of photography who changed the perception of Vogue, such as Irving Penn and Richard Avedon and, in today’s world, Innez and Vinoodh. She then discusses the Naomi and Nadja Auermann shoot and how she suggested having them stand in a field to create the iconic grunge look.

Taking a trip down memory lane, Anna delves into the Vogue archives to discuss a number of her most famous, iconic, and memorable covers. She breaks down her decisions and how those decisions helped evolve the Vogue brand. She starts with her very first Vogue cover shoot and goes through iconic Vogue cover shoots to show the necessity of constant change and bold moves to make a fashion statement.

Anna has launched the careers of some of fashion’s most world-renowned designers. She talks about what makes a designer stand out and gives essential tips for surviving as a creative today.

The world of fashion is ever-evolving, and it can be challenging to stand out and make your mark. Anna takes you behind the scenes of the 2018 CFDA/Vogue Fashion Fund, where she reveals what the judges look for in new and upcoming talent, and she advises on how to help designers and creatives succeed.

Anna highlights what has made these creative leaders successful by telling the stories of Christopher Bailey, Miuccia Prada, and Michael Kors.

In her final lesson, Anna discusses the deeper meaning of her work and why crediting others is always important. She explains that iconic leaders don’t just execute their jobs; they also build relationships with their audience and take a stand.

Key Points I am taking away from Anna Wintour’s Class:

I cringe at the idea of criticism. If I hear one negative comment about my designs, you better believe that I am going to scrap the whole project. Anna has dealt with far more criticism in her life and still comes out on top. The idea is to stay true to your vision and let your work speak for yourself. It is advice I will definitely remember forever.

As a fashion, I just focus on creating unique and breathtaking designs, but so far, I never had to collaborate with a team of people actively. Anna explains that sometimes what looks good in theory looks downright awful in person. To avoid that, all you need to do is cohesively collaborate with your team to come up with pieces that look good on camera.

The standard interview process involves lying and faking interests. Anna says that such applicants are always transparent and easy to read for the interviewers, and they almost never get hired. As someone who has taken thousands of interviews, I am sure that she knows what she is talking about. I learned that if I want to stand out, I need to be myself and stay true to my roots. 

My most important takeaway would be to take inspiration from my surroundings. We habitually overlook the mundane and chase something new and exciting. Anna taught me that a true mark of excellence is transforming something dull into something refreshing and exciting. Also, you can always take inspiration from history, as history always repeats itself when it comes to fashion. 

What did I Like about Anna Wintour’s MasterClass?

Here’s what truly captivated me about Anna Wintour’s MasterClass – this was not your typical “how-to-be-fashionable” guide. Sure, I learned invaluable tips on developing a signature aesthetic and translating trends into wearable designs. But what truly resonated with me were these unique aspects:

The Business Behind the Bob: Fashion magazines are glossy havens for any fashion designer, but Wintour’s course helped me understand what is required to achieve that level of perfection. Anna is much more than her iconic. She is a shrewd businesswoman who knows the art of brand building, how to navigate a competitive market and the power of leveraging new media to expand reach. Vogue is not just a magazine but a global brand, and understanding its business side will give it a massive advantage in the future.

From Runway to Retail Reality: As a designer, my mind often wanders into a world of flowing fabrics and fantastical creations. Wintour’s MasterClass offered a much-needed dose of reality. She explored the importance of understanding the commercial side of fashion—production costs, target markets, and the delicate dance between creative vision and wearability. It felt like learning the insider trade secrets that would help me transform those runway masterpieces into something that could hang in a store (and sell!).

The Wintour Work Ethic: To be honest, the fashion world is notoriously demanding, and almost everyone knows the challenges that come with it. But Anna Wintour’s MasterClass explored more profound concepts than just glamour; it was about the relentless work ethic that fuels success.  She emphasized the importance of focus, unwavering attention to detail, and the ability to make tough decisions. It was a refreshing dose of reality, a reminder that achieving creative excellence takes more than just a good eye for style.

Beyond the Runway: One of the biggest surprises for me was the applicability of Wintour’s lessons across industries. Her insights on building strong teams, fostering innovation, and maintaining a clear vision resonated deeply. Her leadership principles are not confined to the pages of Vogue; they are transferable skills that are valuable for any aspiring creative leader.

Anna Wintour’s MasterClass was not just about transforming my dorm room sketches into a coveted runway collection (although a girl can dream!). It was about igniting a fire within, a belief that even the most outlandish designs can succeed with a strategic plan, a relentless work ethic, and a healthy dose of focus.

Anna Wintour MasterClass Review Conclusion

So, did Anna Wintour’s MasterClass catapult me from a fashion-obsessed student to a couture connoisseur overnight?

Well, I assume the path from dorm room mood boards to presenting at Paris Fashion Week likely involves many more muslin prototypes and late-night sewing sessions than this course offered.

But here’s the thing: that was not why I took this class anyway. My point was not about a shortcut to fashion fame but acquiring the tools and inspiration to transform my fashion fantasies into a focused creative pursuit.

Anna Wintour’s MasterClass was not about memorizing the seven different types of pleats (although that knowledge is now permanently lodged in my brain). It was about peering behind the curtain of Vogue and understanding how Wintour curates a magazine that feels both timeless and relevant, a platform that launches trends and shapes conversations.

Suddenly, the idea of crafting a fashion line that was not just trendy but spoke to a deeper cultural narrative stopped being just a dream; it was a path paved with research, strategic planning, and a whole lot of Wintourian inspiration.

Compared to other fashion designing courses and tutorials out there, Anna Wintour’s MasterClass hits different. I did not learn much about sketching techniques or the latest runway trends. But I surely knew about the business acumen needed to navigate the fashion industry, the importance of building a strong brand identity, and the unwavering focus that separates a fleeting trend from a true fashion moment.

Sure, you can find tutorials on sewing techniques anywhere, but learning how a powerhouse like Wintour approaches trend forecasting, team management, and the ever-evolving media landscape – that’s a golden nugget of knowledge.

So, is Anna Wintour’s MasterClass worth it?

The answer to that question is a resounding YES (aggressively nods her head)!

For aspiring fashion designers, curious enthusiasts like myself, and even seasoned industry professionals looking for a fresh perspective, this MasterClass is a treasure trove of knowledge and inspiration.

It is a masterclass in creativity, leadership, and the unwavering belief that fashion is more than just pretty clothes; it’s a cultural conversation waiting to be designed. And who knows, maybe with enough dedication, a sprinkle of Wintourian wisdom, and a whole lot of passion, my sketches will evolve from dorm room dreams to designs that grace the pages of Vogue (or at least a trendy boutique window!).

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