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01

ANNA WINTOUR

Introduction

Journalism is in Anna Wintour’s blood. or contractions. Most recently, in 2019, Anna


From the time she was a teenager in London, was named Global Content Advisor—in this
her father, Charles Wintour, longtime editor of new role she assumes over sight of Vogue
the British newspaper The Evening Standard, International, a central hub that creates digital
would consult with her on how to make the paper content for Vogue titles around the world. She
more appealing to a younger demographic. also will advise the executive leadership team
She began her career in 1970 as an editorial on global content opportunities and act as a
assistant at Harper’s & Queen then moved to resource to Editors-in-Chief and editorial talent
New York in 1975 and worked for the American worldwide.
edition of Harper’s Bazaar before becoming Anna received her Officer of the Order of the
fashion editor of New York magazine in 1980. British Empire in 2008, and in 2017 she received
In 1983, when she was only 33 years old, her Dame Commander of the Order of the British 2

Anna was hired by Alexander Liberman, Artistic Empire. She also received the French Légion
Director of Condé Nast, as Creative Director d’Honneur in 2011. Over the years Anna has lent
of American Vogue under then Editor-in-Chief, her name, resources, and time to many philan-
Grace Mirabella. Shortly after, Anna returned thropic endeavors, including the CFDA/Vogue
to England to become Editor-in-Chief of Fashion Fund, Youth Anxiety Center at New
British Vogue, only to return to New York in York-Presbyterian Hospital, and God’s Love We
1987 to take over House & Garden. Less than a Deliver. However, it’s her enduring commitment
year later, she became Editor-in-Chief of to the Metropolitan Museum of Art that’s sure
American Vogue, a position she’s now held for to be a leading pillar of her legacy. In 2014,
more than 30 years. then First Lady Michelle Obama personally
In 2013, Anna was appointed artistic direc- performed the ribbon cutting at the opening of
tor of Condé Nast, meaning she oversees the the Anna Wintour Costume Center. Anna serves
creative direction of all of the titles in the compa- as a trustee of the museum, and she has raised
ny’s portfolio except for The New Yorker and is more than $231 million for the Costume Institute
involved in corporate decision-making, such as through her reinvention of its annual gala.
shifts in digital strategies and brand expansions Welcome to Anna Wintour’s MasterClass.

MASTERCLASS
02
ANNA WINTOUR

Getting the Work Done:


Anna’s Management Tips

anna’s tips

Hire and build a great team

Build a system for keeping track of your work

Give feedback quickly and be direct

Don’t micromanage

Be thoughtful about how you run meetings and why

“Not everyone is going to agree with you.” If you trust your team, you can avoid micro-
Anna believes that once you accept this and managing. This doesn’t mean Anna isn’t 3

resolve to stay true to your own vision, you can be detail-oriented—she reads every word that
a better leader and manager. Having strength of goes into the magazine and approves every
conviction and communicating your point of view look for fashion stories—but she also empowers
with clarity and decisiveness is the core compo- her editors to make decisions on her and the
nent of Anna’s leadership style. This applies both brand’s behalf. 
to what Vogue shares with its audience as well In this chapter Anna advises on how to hire
as to how Anna interacts with her team. Hiring and how to communicate clearly and directly.
team members who are self-reliant and diverse She also explains her daily routine and how to
in their way of thinking and observing the world is be most efficient with your time. Anna is hyper-
key and allows Anna to delegate confidently and organized and scheduled, which allows her to
trust those working for her. remain responsive and available to her team.

MASTERCLASS
02 / Getting the Work Done: Anna’s Management Tips ANNA WINTOUR

HOW ANNA GETS IT DONE


MORNING PERSON MEETING MINUTES OUT AND ABOUT THE “TAKE
Anna wakes up between Arriving at the office Throughout the day Anna HOME BAG”
4 a.m. and 5 a.m. and between 8 a.m. and 8:30 will often have meetings You’ll need a system for
reads the British and a.m., Anna’s day typically outside of the office, at the staying on top of things
American newspapers consists of various meet- Met or designers’ studios. that works for you. Anna,
(The New York Times, The ings ranging in size and Even so, she makes a point for example, has the “take
Wall Street Journal, The intimacy, from one-on-ones of responding quickly to home bag”: At the end of
Guardian), looks at Twitter with editors in her office emails and queries from her each day, the take home
and Instagram, exercises to fashion and features entire Vogue team to keep bag is filled with a variety
(usually tennis), responds meetings with up to 40 things moving forward.  of things that need Anna’s
to emails, and mentally people. Anna prefers small feedback or approval,
maps out her day.  meetings—they tend to be including “the book,” a
most efficient—but larger mock-up of the issue that
meetings are an important is currently in production.
time for everyone to get on Anna goes through the
the same page.  book every night and
comments on it with Post-it
notes. She then goes over
her notes with the art
department and editors
the next morning. The take 4
home bag will also include
drafts of articles for upcom-
ing issues, pitches for future
stories, photographer or
stylist portfolios, invitations,
and scheduling questions. 

BUILDING A STRONG TEAM


DIVERSIFY FIND A TEAM YOU TRUST
When it comes to building your busi- Find a self-starter: someone who can
ness, your team should be as diverse make decisions on your behalf and
as possible—different backgrounds, who’s going to be a good ambassador
“You are nothing experiences, ages, and opinions. Hire for you and your business. Groom
without a good team.” with the goal of covering your blind them to be collaborators by empower-
spots: Surround yourself with people ing them to make leadership decisions
who will inform the judgment calls you on their own. You’re investing time
make and the content you put out. and resources in this person, so
consider their potential for longevity at
your company.

MASTERCLASS
02 / Getting the Work Done: Anna’s Management Tips ANNA WINTOUR

WEEKLY MEETINGS AT VOGUE


FASHION SCHEDULING WEB FEATURES
Everyone who works in A smaller group of fashion, Each section editor Features and web
fashion (about 40 people features, and art editors (Fashion, Runway, Culture, meetings are held back-
across the title) meets to go meet weekly to discuss any Living, Beauty) goes over to-back, which means
over the fashion schedule upcoming fashion and what stories they have that print and digital
and discuss general feature stories for the next slated for the coming section leads are present
updates, recent collections, few issues. These stories week. Up to 200 stories for both. This allows for
changes in the industry, go in the “well,” or middle are published on Vogue. seamless integration and
trends, and any other of the magazine (where com across all verticals collaboration between the
fashion-related news. the longer articles and each week, from hot takes magazine, the website, the
the multi-page fashion on pop culture (“The social team, and the video
photoshoots reside). First Trailer for Joaquin team, which has become
Scheduling is perhaps the Phoenix’s Joker Is the Stuff increasingly important as
most important meeting of of Nightmares”) to politics more and more readers
the week: It confirms that (“12 Things to Watch for are consuming their media
everyone—print editors, During the Democratic digitally. All teams work
digital editors, social Debates”) to makeup closely together and lean
media managers, video coverage (“The Best on one another heavily,
producers—is operating Cream Blushes to Wake with the web team publish-
in sync. Whether they’re Up Your Skin This Fall”). ing the print magazine’s
discussing a photogra- Less than 5 percent of articles—often before the 5
pher’s availability for a those stories come from the print issue comes out in an
story or who the best team magazine, and the remain- effort to tease a high-pro-
would be for a cover shoot, ing 95 percent are original file story or cover—and the
this smaller meeting allows content. print editors considering
all topics to be discussed which pieces will perform
openly and resolved swiftly. well online. The executive
When planning your own editor, Anna’s number two
meetings, focus on what in the features department,
the goal of the gathering is, leads the features meeting.
then plan the meeting’s size This consists of going over
and schedule accordingly. the features schedule and
addressing the timing
of upcoming stories,
reviewing where writers
are with their deadlines,
and discussing future story
ideas. 

MASTERCLASS
03
ANNA WINTOUR

Starting Out: Finding Your


Voice and Succeeding

anna’s tips

Learn. Watch. Work hard.

Get off your phone and be inspired by the world

Be daring and take risks

Be thoughtful when you ask for help

W h e n i t c o m e s t o yo u r c a r e e r , decisions. Her confidence to push limits was


it’s important to know what you want and born out of never having anyone tell her “no” 6

have a strong sense of your goals. But in those early years, and she recommends
that shouldn’t prevent you from “Try different that you approach decision-
experimenting. Sometimes the best making with that same sensibility.
things—it’s almost
way to discover what you want to If you are at the beginning of your
more important to
do is by doing things you don’t want career, think about how you can
to do. Anna started out as an edito- find out what you use your early jobs to diversify your
rial assistant at Harper’s & Queen don’t like rather than skill set, build the confidence to
in London, where she was exposed what you do like.” take creative risks, learn as much
to every facet of the editorial process due to as possible, and, bottom line, try everything.
the publication’s small staff and tight budgets. Anna emphasizes the importance of working
This range of experience helped her discover for others at the beginning of your career rather
the roles she was passionate about and well- than trying to make it on your own. Finding a
suited for as well as the ones she wasn’t inclined leader whom you admire and, ideally, look to
toward (such as styling fashion shoots). as a mentor is as important as finding a job
The freedom and flexibility that came with that appeals to you. Do your research, and try
working for an understaffed publication made to work for someone who will push you and help
Anna feel empowered to make bold editorial you develop into a future leader in your field.

MASTERCLASS
03 / Starting Out: Finding Your Voice and Succeeding ANNA WINTOUR

You may not be able to choose who you work for, whose career you hope to emulate may
but you can keep your wants in mind when you lead to other opportunities. And even if your
are interviewing and applying. Look for jobs boss does not become your mentor, glean as
in which you’ll be under someone you respect— much insight and knowledge from them as you
you may not want to be an assistant, but can and take that information with you into your
the opportunity to support an industry leader next position. 

FINDING YOUR VOICE


HEADS-UP OVERTIME SEARCH PARTY
Don’t keep your head buried in your Your work and life interests should Always be on the lookout for things
phone or computer. Listen to others, intersect enough so that they begin to that interest you and know that these
and explore the real world. inform each other: When you’re out of things can come in the most unex-
the office, be thinking about the ways pected places—from an Off Broadway
the book you’re reading or the film show to an exhibition at a gallery you
you’re watching can inform your work; wandered into.
conversely, when you’re at work, try
drawing on inspirations from the other
areas of your life.
7

INTERVIEWING FOR  A JOB


TELL THE TRUTH BE PREPARED BE ON TIME BE YOURSELF
Let’s say you know that Do your research about In fact, be early—it’s the Authenticity is key—
your interviewer loves the the job you are applying best way to make a good whoever is interviewing
theater. Unless you really for and the person you are impression. you will know if you are
love the theater and can interviewing with. Know posturing. Be direct and
rattle off your favorite what your goal for the very clear about what it
shows, don’t try to impress interview is and what you is you want to do with
him or her by discussing think you would contribute your life.
subjects that you’re not to the position you are
actually interested in. interviewing for. 
Chances are you’ll end up
sounding disingenuous. 

MASTERCLASS
03 / Starting Out: Finding Your Voice and Succeeding ANNA WINTOUR

LEARN MORE: AHEAD OF HER TIME


Katharine Graham was one of the first female publishers of
a national daily newspaper. She led her family’s newspaper,
The Washington Post, for more than two decades, fearlessly
overseeing the publication as it broke the news of the
Pentagon Papers and the Watergate scandal. She was the
first female CEO of a Fortune 500 company. In addition to
being a formidable business leader, Graham was a leader
of Washington society and a renowned hostess.

Recommended Reading and Viewing

Personal History, by Katharine Graham 8


The Post, directed by Steven Spielberg
All the President’s Men, by
Bob Woodward and Carl Bernstein
All the President’s Men, directed by
Alan J. Pakula

MASTERCLASS
04
ANNA WINTOUR

Inside Vogue:
Leading With a Vision

anna’s tips

Own and be clear about your vision

Lead your team with a strong point of view

Study the world and absorb what is happening culturally

Be open to hearing others’ perspectives

Give your team members projects they are passionate about

In addition to generating $1.9 trillion work for you to approach the world with a criti-
in revenue annually, the global fashion industry is cal eye. For Anna, this means sending her writers 9

a vital reflection of our culture and has the ability and editors out into the world, where they can
to capture the zeitgeist in a unique way. It is up to do boots-on-the-ground reporting and observe
Vogue to place fashion within and react to what they see.
the context of the wider world. “Watch the world, study They then bring those expe-
This chapter outlines the shifts in culture, and listen riences and sensibilities back
trajectory of a fashion edito- so you can make choices that to their work and decide if
rial at Vogue, from a collec- speak to what is happening and how something should
tion’s debut on the runway to in a wider context. That, be covered in the magazine.
the fashion meeting in which to me, is what a leader does.” Vogue focuses on the world
editors discuss how best to of fashion, but the lessons for
interpret the themes of the collection to the final a creative leader are the same no matter what
clothing choices for both digital and print shoots. your business’ focus is. Keeping your eyes and
Anna and her team focus on the intersection ears open to the world around you and encour-
of fashion and culture, but no matter your indus- aging your deputies to do the same is an essen-
try, it’s important to encourage the people who tial quality for a leader in any industry. 

MASTERCLASS
04 / Inside Vogue: Leading With a Vision ANNA WINTOUR

FROM RUNWAY TO RUN-THROUGH:


THE EVOLUTION OF A FASHION STORY
FASHION FEEDBACK POINT OF VIEW RUN-THROUGH
A fashion meeting is held weekly Anna goes over all the ideas with After the fashion stories have been
at Vogue, but the most important her team. Together they decide assigned to fashion editors, the
fashion meetings take place imme- which stories make sense for which fashion market team will collaborate
diately following the September and platform­—whether a story should go to put together “boards,” which
February month-long line-up of on the website or into a video, whether feature images of select looks from
fashion shows across the globe. In it’s framed as social-first, whether it the collections. Not unlike a mood
addition to New York, London, Milan, should be held for forthcoming issues, board, these also feature visual
and Paris, Vogue now sends editors or whether it merits a combination of inspirations for the story, including
to emerging fashion capitals such these approaches. Scheduling is also reference images from other shoots,
as Lagos, Nigeria, Tbilisi, Georgia, discussed, as well as which editor is photos of the location, and pictures
and Tokyo, Japan. When Anna and handling what. This is when Anna of the model. The last step before
the editors return from the various and her team decide how Vogue will the shoot is the “run-through.” In the
shows, she asks everyone to send digest and reflect what was seen on days leading up to the shoot, after
ideas for future Vogue fashion stories the runways and what their point of the concept and boards have been
inspired by what they have seen on view will be in their depiction. The approved, the fashion editor will come
the runways (beauty trends that have general story ideas are chosen based into Anna’s office with a rack of the
emerged, up-and-coming designers, on the ideas previously sent to Anna selected clothing pieces and photos
particularly visible models, etc.). The by each editor, then the details are of the models or celebrities in each
10
team will have seen over 150 collec- fleshed out based on the feedback look (if their schedule permits, most
tions between all of the shows, so this from this meeting. It is a lively, collabo- models or celebrities will come in to
is a way to distill a surfeit of informa- rative effort that encourages discus- the Vogue offices for a fitting ahead
tion and make sure nothing important sion and creative thinking. No matter of the shoot to make sure the clothes
is lost. If you’re having to manage what industry you’re a leader in, it’s fit and look the way the editors and
many creative outputs as part of your crucial that you don’t just regurgitate Anna want them to). The attendees
job, it’s essential to find a system for what you see, hear, or read. Rather, typically include the fashion editor (in
keeping track of all the information take in that information, cogitate on this scene, Alex Harrington), creative
you gather and then finding the best and process it, and then decide what Director, Raúl Martinez, sometimes
way to digest that information.  it means. This will result in projecting a fashion assistant or market editor,
a unique point of view. and, of course, Anna. Anna is
  unerringly direct and clear in feedback.
“It’s very important that I lead my team with a That is always in balance with the
creative decisions she empowers her
point of view and that we absorb and reflect what
team to make. Similarly, it’s important
is happening in fashion and the larger culture. But to be clear with yourself and your
it’s also very, very important to listen to other per- team on which decisions need your
final call. Clarity, striaght-forwardness,
spectives. I think one’s final direction and point of and honesty are traits that are of
view is always stronger when you have listened to critical importance for any leader. 
your team and to those around you.”

MASTERCLASS
04 / Inside Vogue: Leading With a Vision ANNA WINTOUR

LEARN MORE: FASHION EDITOR VS. STYLIST


These terms can be interchangeable, but that isn’t always
the case. A fashion editor is responsible for the look and
mood of the shoot, be it for Vogue or Vogue.com; he or she
chooses a photographer, the clothing, the location, and the
models. A stylist will sometimes do all of this, but the term
can also refer to someone who is choosing the clothing for a
digital or print shoot, or possibly a public appearance. 

Recommended Reading and Viewing

11
In Vogue: The Editor’s Eye,
directed by Fenton Bailey and Randy Barbato 
Vogue: The Editor’s Eye,
by Eve MacSweeney and Hamish Bowles
Grace: A Memoir,
by Grace Coddington
Grace: Thirty Years of Fashion at Vogue,
by Grace Coddington
Stoppers: Photographs From My Life at Vogue,
by Phyllis Posnick 
Point of View: Four Decades of Fashion,
by Tonne Goodman

MASTERCLASS
05
ANNA WINTOUR

Editorial Decision-Making

anna’s tips

Always try to create something original that has meaning

Provoke a conversation

Make mistakes (they’re inevitable) and then learn from them

Let data inform you, not lead you

D u r i n g h e r e a r ly y e a r s at v o g u e , The shoot featured Kim in various wedding


Anna was seated next to a businessman on dresses and hit newsstands a few weeks before 12

a transatlantic flight who explained how much the pair’s Tuscan wedding. The cover was a reac-
he loved the magazine because of its elegance tion to a specific moment in the zeitgeist, thus
and stylishness—for example, he said, you would keeping Vogue at the center of a larger cultural
never see Madonna on the cover of Vogue. conversation.
(Madonna was seen as edgy and risqué, Conversely, Anna admits that some bold
not elegant and well-be- choices may lead to critiques that
haved like the typical “Vogue “You are leading. are warranted. In August 2017,
girl.”) His comment stayed You are not following.” she made the decision to put
with Anna; a few years later, model Gigi Hadid and her then
it was one of the things that pushed her to boyfriend, Zayn Malik, on the cover, with Gigi
do away with the rule book and instead in menswear and Zayn in what some would
respond to a cultural moment: In May 1989, consider more traditionally women’s clothing.
Madonna got a cover.  The Internet took umbrage with the fact that
The same would be true 25 years later with Anna chose a heterosexual couple—rather than
Kim Kardashian and Kanye West, who graced a gender-fluid couple—for such a shoot. Anna
the cover in April 2014. Vogue, and specifically noted the criticism, and Vogue apologized. It is
Anna, endured a lot of criticism for that decision. of vital importance to own your mistakes.

MASTERCLASS
05 / Editorial Decision-Making ANNA WINTOUR

Over the course of your career, you’ll inevi- evaluate whether those decisions are the
tably have to decide if and when to make bold right call for your brand. Anna recalls some-
creative choices. Anna outlines her strategies on thing Ralph Lauren once said to her about his
when to break the rules and do the unexpected. company: “I don’t want to be too hot, and I don’t
There is a Goldilocks element to toeing the want to be too cold,” he said. “I just want to
line between risk and reward, conversation- be part of the conversation.” Anna has always
starting controversy, and blatant offense. For worked hard to make sure Vogue remains an
example, putting runway images on a cover in integral topic of discussion. If you want to be an
1993 was a major risk that Anna later admit- influential creative leader who makes their mark
ted was a mistake. By understanding the larger on the world, you will have to do the same in your
implications of certain decisions, you can own work.

TAKING SHAPE: FROM PITCH TO PRESS


INSPIRATION AND IDEAS PIECING THE PUZZLE TOGETHER
Anna shows how important it is to be both generative and After story pitches have been approved by Anna, she
reactive by inviting you into the Vogue features meeting as discusses with the rest of her team whom the best person
the team is planning for the March 2019 issue. After observ- would be to write, photograph, and style each story and
ing the runways overseas, the team returns from Europe whether the story should debut in the magazine or run
inspired to focus on the power of the West Coast, and immediately online. The editors will then work with the 13
specifically California. The editors then synthesize fashion individual writers, and Anna will give her feedback on the
trends they saw on the runway with much bigger themes edits; the same goes for the fashion editors and photog-
and cultural currents: Seeing a rush of neoprene and tie- raphers. Once the images and the articles come in, they
dye on the runway, for example, evoked thoughts about are laid out in miniature on a four-by-six-foot magnetic
the importance of surf culture, seaweed foraging, sustain- board so Anna can see how all the images and articles look
ability, and the emergency crews who responded to the together. Getting the right mix of information is as import-
California wildfires. With all these subjects being considered, ant as the individual stories. If something feels off in any way,
the issue’s focus and digital coverage turns to California’s a story might be held for a later issue, or an image will be
impact in a number of realms, from art and politics to tech swapped for a different one. There will always be data and
and fashion. numbers to help inform how best to appeal to your target
demographic, but Anna believes that trusting your instincts
and having a passion for your audience is vital. It’s better
to be engaged in the world around you and digest what
you see than bury your head in spreadsheets. Both can
be valuable, but it’s your intuition and unique perspective
that will distinguish you as a leader in your field. The Vogue
features meeting is a great example of how your work needs
to always reflect a bigger picture. As a creative leader, how
does your work connect to the culture? Are you leading the
conversation or playing catch-up?

MASTERCLASS
05 / Editorial Decision-Making ANNA WINTOUR

LEARN MORE: KOURTING KONTROVERSY


Anna knew that Vogue’s cover featur- they admired. Anna had to defend the
ing Kim Kardashian and Kanye West magazine against criticism that
would ruffle feathers, so she took it had devolved into US Weekly,
precautions to keep it a secret until going as far as publishing letters to
publication (often the identity of an the editor in the following issue with
upcoming cover subject can be leaked claims of readers being “speechless”
to the press before the issue’s official and “disappointed.” The media
publication date). reaction was vicious: Magazines
like Elle and Cosmopolitan published
The Kardashian-West cover was snarky web posts about the choice,
divisive for a number of reasons: even though they would all go on
First, many loyal readers didn’t feel to feature Kardashians on their
as though it reflected the elegance covers. However, Anna and Vogue
for which Vogue has come to be weathered the noise, and it has
known. (Think of it as a nouveau- since become one of the most
Madonna cover.) In fact, many memorable issues in the magazine’s
felt it was a betrayal by a title recent history.

14

MASTERCLASS
06
ANNA WINTOUR

Executing a Vision:
Transforming the Met Gala

anna’s tips

Build a vision others can believe in

Nothing extraordinary happens overnight. Great things take time.

Attention to detail is critical

Build excitement and think about how you can engage the widest possible audience

Fou n d ed i n 1870, t h e M e t ro p o l i ta n she and Vogue would consider helping


Museum of Art is one of the most famous with the event. She accepted.  15

museums in the world. Its Costume Institute, A quarter-century later, Anna has turned the
which focuses on fashion history and Met Gala into the biggest event of the year, with
artistry, often finds itself in the spotlight celebrities and power brokers eager to attend.
thanks to its annual Costume Anna emphasizes that the
Institute Benefit (you might “Sometimes a big vision event’s growth did not happen
know it as the Met Gala). overnight, noting that two
and bold initiatives take
What started as a midnight of the most important qualities
time. Things do not
supper in 1948 has since a leader can have are patience
turned into a massive fund- happen overnight.” and diplomacy. Anna had her
raiser for the Institute’s exhibi- own ideas for the event, but
tions and acquisitions; over the years, the she knew she had to be patient and respect-
gala has boasted co-chairs as famous as ful in bringing those to fruition. If you’re in the
Jacqueline Kennedy Onassis and socialite position to spearhead a branded event, Anna
Patricia Buckley. In 1995, Oscar de la Renta would encourage you to start by taking the
and his wife, Annette, a trustee at the long view, being patient with your partners, and
museum, approached Anna to ask if proving the value you bring to the project.

MASTERCLASS
06 / Executing a Vision: Transforming the Met Gala ANNA WINTOUR

GOOD THINGS COME TO THOSE WHO PERSEVERE


OPPORTUNITIES COME IN UNEXPECTED WAYS
When Anna received the call from the de la Rentas, she
never anticipated what she would be taking on or what it
would become.

BEING A LEADER IS ABOUT RESPECTING


OTHER LEADERS
The Met is a historic institution with a long history and
a strong point of view. In order to bring about change
in the way the Met Gala was produced, Anna had to be
diplomatic: She brought partners together, listened to and
understood everyone’s goals, and collaboratively found a
path forward.

Recommended Reading and Viewing

The First Monday in May, directed by Andrew Rossi


16
Vogue and the Metropolitan Museum of Art Costume Institute:
Parties, Exhibitions, People, by Hamish Bowles
Diana Vreeland: The Eye Has to Travel, directed by
Lisa Immordino Vreeland

MASTERCLASS
07
ANNA WINTOUR

The Power of an Image:


Photographers and Models

anna’s tips

Gather references to communicate your vision

Take your audience on a journey

Don’t be afraid to rise to a challenge

Choose models who have personality and presence

Be thoughtful about what your choices say about the message you want to communicate

Don’t be cookie-cutter

Great photographers have the power to photographers, each of whom brings their own
lend transcendent meaning to an image. As Anna point of view and aesthetic to the magazine. It’s 17

says, “One looks to the great photographers—and also important to Anna to find photographers
to the great models who work with them—to give who are invested in representing the Vogue brand
even more impact to the art of the fashion photo- and who tell a story through their images: Their
graph, whether it’s through a narrative or through work should reflect a tangible cultural moment,
a still life or through a portrait.” Although Anna is but the best photographers know how to create
specifically referring to the process of working with an image that will still feel relevant years later.
photographers who shoot for Vogue, the lessons The models who appear on the cover of Vogue
apply to any creative leader: Identify and engage and inside its pages symbolize the values of the
strong talent who understand you and your vision, magazine and the brand. They have to represent
and create work that has relevance and speaks to the current cultural moment but also be timeless
a moment. arbiters of style. Anna explains that a model is
Every issue of Vogue and every video, article, not just a face and a figure; there has to be a
or visual portfolio that appears on Vogue.com soul and a spirit that shines through, and that is
is a study in creating the right mix of images, what makes someone a “Vogue girl.” Think hard
from political portraits to more whimsical fash- about the sensibility and identity of your brand
ion narratives shot abroad. The most important and the best person who can convey that to your
element of that mix is working with a variety of audience through an image.

MASTERCLASS
07 / The Power of an Image: Photographers and Models ANNA WINTOUR

WHAT MAKES A GREAT


FASHION PHOTOGR APHER?
“USE EVERY SINGLE photograph Beyoncé for the cover of are refining your eye and point of
OPPORTUNITY TO HONE Vogue’s September 2018 issue. Don’t view, try different types of photogra-
YOUR EYE” write off a job just because you think phy and be as bold as possible. The
Anna uses the young photographer it’s too small (or too big)—you never more extreme your experimentation,
Tyler Mitchell as an example of know what it may lead to.  the easier it is to identify the DNA
someone who used every opportunity of your imagery.
KNOW WHAT YOU LIKE
to understand his own point of view
Assemble a collection of images that BE PREPARED
and fashion’s point of view. When
speak to and move you. Once you Annie Leibovitz, like Irving Penn before
he was coming up, he’d photograph
have a sizable collection, you’ll start to her, scrupulously prepares for photo
everything from events for Vogue.com
identify themes and a shared sensi- shoots before she ever picks up her
to the line outside the Supreme store. 
bility, which will help hone your own camera. She will always study her
WORK YOUR WAY UP TO THE aesthetic behind the lens. subjects beforehand, which could
BIG LEAGUES mean seeing the play they’re in or
BE BOLD
No assignment is too small when reading their latest book. Penn was
“We’re looking for somebody that takes
you are learning and building your the same: He’d spend time getting to
pictures in a different kind of way,”
portfolio. At 24 years old, and after know the subjects on set so that the
says Anna, who looks for strength in
working on smaller assignments for atmosphere felt personal and intimate
an image as well as a quality that will
Vogue.com, Mitchell was asked to before the shooting began. 
allow it to resonate over time. As you 18

WHAT MAKES A GREAT CREATIVE LEADER?


KNOW WHAT YOU’RE
LOOKING FOR
When you’re looking for a photog-
rapher, it’s important to keep a
collection of photos that inspire you.
Reference those images when looking
“As a creative leader, the visual medium at photographers’ portfolios.
is so powerful, and photographs are often BALANCING ACT
the most powerful tool to express your There is a delicate balance between
trusting the photographer’s vision but
creativity, to help define your title, and also impressing upon them the specific
reflect a moment in time.” needs of your business. Stand firm in
your creative convictions, lead boldly,
and believe in the talent you hire.

MASTERCLASS
07 / The Power of an Image: Photographers and Models ANNA WINTOUR

WHAT MAKES A GREAT MODEL?


MORE THAN JUST A FACE STANDING FOR SOMETHING
Models should convey the spirit of Models often reflect the pulse of a
your brand. Their approach to the certain time (think Kendall Jenner or
world should mirror yours. There Gigi Hadid today). It’s important to
are many ways to decide whether a find the person who encapsulates
model has the right sensibility for your the current moment and who has a
content, be it print, video, or digital, passion for what they do. It’s also
but meeting them in person is one good if they have outside interests,
important step. A casual conversation hobbies, and opinions. You want
face-to-face (or via FaceTime) can someone whose spirit jumps off the
go a long way toward figuring out page.
whether someone is the right fit. Ask
BE OPEN TO SOMEONE
them questions, and see for yourself
BREAKING THE MOLD
whether they have strength of convic-
Some of the best models—Iman,
tion and strong points of view. 
Naomi Campbell, Ashley Graham—
were the first of their kind in one way
or another. Prescient editors saw the
value in those models’ uniqueness and
highlighted it. 
19

Recommended Reading

Irving Penn: A Career in Photography, by Colin Westerbeck, Colin Eisler, et al.


Horst P. Horst, by Susanna Brown 
Richard Avedon: Photographs 1946–2004, by Michael Holm et al.
A Photographer’s Life 1990–2005, by Annie Leibovitz

MASTERCLASS
08
ANNA WINTOUR

Evolving a Brand:
A Look Back at Iconic
Vogue Covers
anna’s tips

Make your mark, especially when starting a new role

Always keep your antennae attuned to cultural shifts

Trust your team and be open to surprises

Channel the cultural conversation around your work

Believe in your instincts and execute on them

People expect change

Anna walks through some of her cover


decisions from the past 30 years to illustrate 20

how to make strong creative decisions and


maintain the vitality of a historic brand without
“As a leader for your company,
alienating your core audience. 
you will be tasked with making
larger strategic creative choices
that help evolve how the audience
understands your brand. Your
brand has to be at the core of all
your creative decisions. What is
it? What does it stand for? How do
you move it forward?”

MASTERCLASS
08 / Evolving a Brand: A Look Back at Iconic Vogue Covers ANNA WINTOUR

HOW TO MAKE BOLD CREATIVE DECISIONS


EXPECT THE UNEXPECTED BE GENERATIVE AND REACTIVE “WHEN YOU COME ACROSS
Anna’s first American Vogue cover In addition to creating new ideas and GREAT TALENT, LET THE
was very different from those that concepts that will set the cultural MASTER LEAD.” FIND GOOD
preceded it: The photo crop was barometer, it is equally important COLLABORATORS.
wider; the model was not looking to take stock of what is happening Good collaborators can come in any
directly at the camera; the clothing around you and react to it (as Anna form. For Anna, it is important to
had a casual sensibility, mixing a did with an issue featuring items feature a cover subject who is eager
Christian Lacroix couture top with under $500 when the economy was and engaged with the process. She
Guess jeans. In other words, it made suffering in the ’90s). Sometimes it’s uses Sienna Miller and Lupita Nyong’o
a statement and spoke to what Anna about working with the trends you are as examples of perfect subjects: Miller
wanted to convey, which was that seeing culturally: Take, for instance, was game to traipse all over Rome in
fashion can be accessible, sponta- Anna’s choice in the early aughts the fall collections despite a heat wave,
neous, and fun. Ironically, that partic- to start featuring celebrities rather and Nyong’o arrived to her fitting with
ular photo was never intended to be than models on Vogue’s covers. At mood boards and suggestions for
a cover. But as soon as Anna saw the that time, actresses were starting to featuring African designers. A fashion
image, she realized its potential and engage with fashion more and more, editor or photographer can also
pivoted accordingly. When you are which is why Anna and her team felt surprise you with their vision, as was
in a new position, it’s important to they made sense as cover subjects. It the case when Irving Penn shot Nicole
find opportunities to communicate to then became cyclical. As celebrities Kidman or Tonne Goodman turned
others what your vision is and what saw their peers getting attention Rihanna into a modern-day mermaid.
type of leader you are going to be. in a positive way from the fashion Collaborating effectively can also 21
press, they themselves became more mean accepting advice from people
“YOU JUST HAVE TO LEAD
engaged with fashion and designers. you trust, as was the case when Oscar
FROM THE HEART.” FOLLOW
It might be hard to imagine today, but de la Renta called Anna to suggest
YOUR INSTINCTS.
back then it was considered some- that she put then First Lady Hillary
For Anna’s first September issue
what radical to put Hollywood stars Clinton on the cover of the December
cover, in 1989, she featured Naomi
on the cover. Anna and the magazine 1998 issue. 
Campbell in a sequined pantsuit
received a lot of criticism and push-
because Anna felt Campbell “repre- DON’T GET STUCK IN YOUR
back, but she knew it was the right
sented everything that was happening OWN WAYS
decision based on the wider influence
in fashion at that time.” Some at Challenge yourself to consider
celebrities were starting to have in
Condé Nast questioned her decision— whether there is a smarter way to be
popular culture.
there was concern that an African doing something. When Vogue began
American model would not sell well on posting its cover stories online in 2010,
newsstands—but Anna ignored them there was concern that the website
and followed her instincts. might “scoop” the print edition (and
thus rob the magazine of newsstand
sales). By experimenting with different
timing, though, Anna and her team
learned that there was great benefit
in posting the cover online early
because it created hype around the
forthcoming issue and appealed to a
wider audience. 

MASTERCLASS
08 / Evolving a Brand: A Look Back at Iconic Vogue Covers ANNA WINTOUR

LEARN MORE: HOW A VOGUE COVER IS SELECTED


Anna and the editors discuss cover choices up to six months
in advance and decide what each cover should be based on
a variety of factors and questions: 
• Who represents the culture right now, or who do you think
should represent the culture right now?
• Who encapsulates this moment? Who is the person
everyone is talking about or will be talking about?
• Who has interesting projects coming up that we are
excited about and want to highlight?
• Who will be a good collaborator on both the shoot and
Recommended Reading  for the interview?
• Who is a good representation of the Vogue woman
Vogue: The Covers, by Dodie Kazanjian today?

22

U.S. VOGUE COVERS BY THE NUMBERS: MOST FREQUENT COVER STARS

25
lauren hutton
15
claudia schiffer
12
Gisele Bündchen 

8
nicole kidman 5Rihanna
4Beyoncé

MASTERCLASS
09
ANNA WINTOUR

Designers:
What It Takes to Succeed

anna’s tips

Have a strong point of view

Think outside the box

Have a consistent message

Find the right partner

There are many ways to be a successful


fashion designer. Anna outlines how you can 23

succeed in that business, whether it’s by starting


your own brand, working under another designer,
or taking the reins at a historic fashion house. 

“Try something that is the


most extreme, that is the most
creative, because when you’re
doing that, you get to the true
heart of who you are.”

MASTERCLASS
09 / Designers: What It Takes to Succeed ANNA WINTOUR

EVOLVING AS A DESIGNER AND


BUILDING YOUR BR AND
KNOW WHAT YOU WANT GO BIG OR GO HOME BREAK THE MOLD
Not everyone has the same goals. It is important to go as big and bold When considering replacing a
Know yours, and stay true to them as as possible, especially at the begin- designer at a historic fashion house,
you pursue success. Perhaps you want ning of your career. Channel Anna either as the designer coming in or
to be the next Ralph Lauren, and have during her Harper’s & Queen days: as the one hiring them, make sure
stores in every city, and expand into Be fearless and extreme, because it you are not hiring a shadow of the
home goods and even restaurants. will help you hone in on what’s at the departing designer. Instead of trying
Or maybe you want to make beau- core of your brand. That passion and to find someone who will rigorously
tiful, unique clothes on an intimate sensibility are what people will keep uphold the codes of the house, find
scale, such as sisters Kate and Laura coming back to you for and identify as the most brilliant designer available
Mulleavy of Rodarte, whose ethereal, the heart of your brand. and allow them to break those codes
delicate dresses are prized as heir- and create new ones. 
THINK OUTSIDE THE BOX
looms because they are not mass-pro-
Don’t hold a fashion show just
duced. Either way, pursue the avenues SET YOURSELF UP FOR
because everyone else is doing it.
that will get you closer to your goals.  SUCCESS
Hosting an intimate presentation in Many creatives are also business
WORK FOR OTHERS your home or filming a video of the people. Identify your weaknesses, then
It may be appealing to launch your collection might make more sense hire people who excel in those areas.
own brand immediately because you for your brand. Anna points out that Make a five-year plan for the business,
have a large social media following video, rather than runway photos, is 24
then use that as a blueprint as you
or have seen examples of others who a great way to show how the clothes tackle each step going forward. 
have done it successfully. But most move and convey the personality of
people will struggle without having the pieces. Do what is right for you
the experience interning or apprentic- and your vision. 
ing under an established designer or
fashion industry leader.

MASTERCLASS
09 / Designers: What It Takes to Succeed ANNA WINTOUR

A LOOK AT SOME OF FASHION’S BIGGEST NAMES


• Designer Tom Ford and business • On a flight from Florida to New York, • John Galliano is a British fashion
executive Domenico de Sole Lazaro Hernandez slipped Anna designer who was creative director
began their partnership when Ford an airline napkin scribbled with for Givenchy, Christian Dior,
was creative director of Gucci and his phone number and a message. and his eponymous label. He
De Sole was president and CEO of She was so struck by his fearless- now holds that title with Maison
the brand. Together they launched ness that she helped arrange an Margiela. Known for his opulent,
Ford’s eponymous brand in 2006.  internship for him at Michael Kors. narrative-rich collections, he was
When he partnered with his Parsons named British Designer of the Year
classmate Jack McCollough to four times and received an Officer
create Proenza Schouler (the of the Order of the British Empire in
maiden names of both designers’ 2001. 
mothers), Anna supported them
from the beginning, and they were
the first winners of the CFDA/Vogue
Fashion Fund (CVFF) in 2004. 

• When Frida Giannini left Gucci • The Los Angeles–based design • At only 24 years old, Alexander
abruptly in 2015, speculation ran house Rodarte was founded by Wang launched his eponymous 25
rampant on who would replace her. sisters Kate and Laura Mulleavy. label and became known for
The industry was shocked when a The pair specialize in delicate, hipster basics—artfully cut T-shirts
little-known designer on the Gucci otherworldly dresses that evoke that models wore off duty, sexy-
accessories team, Alessandro a beautiful shipwrecked mermaid. but-unfussy dresses. In 2012,
Michele, was awarded the post. Wang took over as creative director
Even more shocking was how he of Balenciaga. He stayed in that
completely turned the brand on its role for three years before turning
head, both subverting the codes of his focus back to his own label
the fashion house but also reviving full-time. 
them in unique and unexpected
ways. 

MASTERCLASS
10
ANNA WINTOUR

Spotting Designer
Talent: CFDA/Vogue
Fashion Fund
anna’s tips

When things feel dark, don’t retreat. Engage and lead with a purpose.

Investing in your industry pays dividends

Nurture young talent, but don’t be afraid to be honest with your advice

T h r o u g h e n gag e m e n t a n d e m pat h y inspired Anna to go to the Council of Fashion


you can learn from tragedy and find unex- Designers of America (CFDA) and ask for its 26

pected ways of supporting the people in your partnership in creating a fund to support emerg-
community. September 11, 2001, fell at the ing American designers in perpetuity.
start of New York Fashion As a leader in the fashion
Week. Naturally, all shows “It was important to me industry, Anna felt she had
were canceled in the wake to create the fund, because a responsibility to help buoy
of the attacks. For many as a leader in the fashion the next generation of design-
young designers, the cancel- industry, I felt that it was my ers. Discovering, advising, and
lation of their show had responsibility to ensure the bolstering emerging talent not
drastic ramifications on only helps ensure the future
future of American fashion.”
their businesses, as many of whatever industry you
had spent all their money securing venues, are in, but it can also inspire you and inform
production, and models. It was a situation that your own work. 
made Anna and her team realize the precar- The CFDA/Vogue Fashion Fund is both
iousness of many fledgling designers’ busi- monetary—winners receive anything between
nesses. As a result, Carolina Herrera opened $150,000 and $400,000—and advisory, with
her showroom to 10 young designers so they each winner being assigned an industry leader
could present their collections. Herrera’s gesture as a mentor. Each year there are 10 finalists

MASTERCLASS
10 / Spotting Designer Talent: CFDA/Vogue Fashion Fund ANNA WINTOUR

chosen from hundreds of applicants. The Wang, Altuzarra, Brock Collection, Tabitha
finalists go through a six-month period of site Simmons, Prabal Gurung, Thom Browne, Derek
visits and challenges as well as presentations Lam, 3.1 Phillip Lim, Thakoon, Jennifer Meyer,
to a selection committee composed of industry and Monique Péan, and its success has even
leaders. The winner and two runners-up are inspired a number of similar global initiatives.
announced at an awards gala in November. The CFDA/Vogue Fashion Fund is an
Vogue helps to prepare the finalists for each important example of how crucial it is to think
of the challenges (creating a look inspired by, beyond yourself in order to be an influen-
say, a favorite film or location) and then aids tial leader and create a lasting legacy. How
them in presenting their portfolio. All of the are you helping support your industry and
finalists are featured in the November issue your professional community? How are you
of the magazine. The program has granted helping foster the next generation? Consider
$5.9 million to more than 35 fashion brands, what your responsibilities are beyond your
including Rodarte, Proenza Schouler, Alexander specific role.

ANNA’S ADVICE FOR FUTURE CFDA APPLICANTS


BE CLEAR BE CONFIDENT BE YOU HAVE A POWERFUL
It never helps you to When meeting the Especially in the video PORTFOLIO 27
obfuscate or exaggerate selection committee, it is submission, be sure to Consistency is key when
the state of your business. essential that you project convey who you are and putting together a fashion
The CFDA fund is an confidence and conviction the essence of your brand. portfolio. Make sure there
opportunity to help you that your business can This is your opportunity to is a unifying spirit among
grow, but applicants succeed among hundreds— distinguish yourself from everything you’re present-
should be clear and honest if not thousands—of other applicants, and the ing, from the images to
about their situation. Do competing fashion brands. stronger your personal and the font to the fabrics.
you have funding? Are you Be prepared to convince brand identity is, the better. Attention to detail pays
profitable? Do you have the judges that you have a So much of selling a brand off because it will help
a scalable business plan? unique selling proposition today is about personal you stand out from the
What is your marketing and know it inside out.  branding, and your crowd; be thorough and
strategy? Have an honest comfort and ability to sell painstaking, but don’t be
answer to these questions yourself behind a camera too complicated or overly
and know where you need will prove indispensable. clever. At the end of the
to improve. day, clarity of vision is
what’s most important.
Show your passion. 

MASTERCLASS
10 / Spotting Designer Talent: CFDA/Vogue Fashion Fund ANNA WINTOUR

LEARN MORE: THE COUNCIL OF


FASHION DESIGNERS OF AMERICA 
The Council of Fashion Designers to hosting the CFDA Awards every
“It’s fascinating to of America (CFDA) is a nonprofit June (think of them as fashion’s
trade organization founded in 1962. Oscars), it manages the New
see that there is no Its mission is to bolster the York Fashion Week calendar. Diane
single path to success American fashion industry and von Furstenberg was the longtime
support American designers. president and then chairwoman,
in fashion.” Its membership includes more than a tenure that lasted from 2006 to
—Emily Bode 500 of the industry’s preeminent 2019. In January 2020, Tom Ford
fashion designers, and, in addition will replace her. 

LEARNING FROM THE 2018 CVFF FINALISTS


Winner: PYER MOSS Runner-Up: JONATHAN COHEN Finalist: REBECCA DE RAVENEL
The takeaway: Respond to your The takeaway: Find a business The takeaway: Don’t be overly
surroundings partner who shares your vision complicated
The six-year-old label founded by Cohen’s eight-year-old line of The ready-to-wear expansion from
Kerby Jean-Raymond seeks to polished-but-cool dresses and the designer of the beloved fabric-
address issues of social justice separates has become beloved by corded BonBon earrings specializes in 28
through fashion. Jean-Raymond uses sophisticated women. Anna was unabashedly pretty, feminine designs.
provocative images and messages on particularly struck by the synchronicity De Ravenel is a good example of
his clothing, creative approaches to of his partnership with Sarah Leff, the someone who is their own best
presentation, and diverse casting to CEO of his company. customer; these dresses and earrings
model his designs. “It’s about giving a look like ensembles she would wear
Finalist: CHRISTIAN COWAN
voice to the silenced,” he says, and his at home in Los Angeles or her native
The takeaway: Be a little extra,
line pushes the boundaries between Bahamas. Trust that what is true to
especially at the beginning
fashion and politics.  you is enough.
Only two years out of Central Saint
Runner-Up: BODE Martins (the prestigious British art Finalist: SCOSHA
The takeaway: Have a unifying spirit school known for its fashion depart- The takeaway: Stay true to your
in all that you do ment), Cowan’s line of over-the-top values
Emily Bode’s namesake menswear glitter suits and metallic dresses with Australian designer Scosha
brand refashions vintage fabrics into princess sleeves have found fans in Woolridge’s eco-friendly jewelry line
modern-day heirlooms. Anna and the celebrities such as Cardi B and Lady is created with old-school metalsmith
members of the selection committee Gaga. Like Anna said, being bold can techniques and inspired by her
were impressed with the harmony that pay off—especially early on, when world travels. Building a sustainable
flowed through Bode’s work, from the you’re still identifying the core of your brand using outdated mechanisms
aesthetic of her studio to her portfolio brand. It will only help you zero in on a presents many more challenges, but
to, of course, her designs.  strong point of view.  Woolridge’s loyalty to her values made
her stand out among other emerging
jewelry brands.

MASTERCLASS
10 / Spotting Designer Talent: CFDA/Vogue Fashion Fund ANNA WINTOUR

Finalist: HUNTING SEASON Finalist: MATTHEW ADAMS


The takeaway: Forging your own DOLAN
path can give you an advantage The takeaway: Don’t be afraid to
The Bogotá-based accessories line reinvent the wheel
designed by Danielle Corona is hand- Classic American sportswear with a
made in Colombia by local artisans. 21st-century twist—oversize blazers,
The sophisticated straw and leather hipster-cut denim—has set Adams
purses draw on that country’s spirit. Dolan apart even though he only
Yes, there are pitfalls to not being launched his brand in 2016. His
based in New York or another fashion fearlessness in taking on simple Recommended Viewing
capital, but building a brand that’s classics shows that they were ripe
authentic to where it was conceived for reinvention.
The Fashion Fund
and created can be invaluable.  
(web series, available on Amazon)
Finalist: BATSHEVA
Finalist: LUAR Seamless,
The takeaway: Embrace the
The takeaway: Try something new directed by Douglas Keeve
unexpected
Raul Lopez’s two-year-old brand Batsheva Hay’s story is an example
caters to everyone: men, women, and of life surprising you: After the
those who identify as gender binary. Georgetown-educated lawyer put
Luar’s vibrant spirit of inclusion her career on hold to raise her two
is similar to one introduced a few young children, she started looking
years earlier at Hood by Air, the for vintage Laura Ashley children’s
transgressive haute streetwear brand clothes on Etsy and found herself
cofounded by Lopez with Shayne 29
wishing there were adult versions
Oliver. Though Lopez didn’t stick of the prairie-style dresses. So
around at Hood by Air, he pivoted she started making her own in
and started over again with his Manhattan’s garment district based
own line.  on patterns she designed and using
vintage fabrics. The demand from
friends and people who saw the
dresses posted on her Instagram
was so high that she started to sell
the pieces. Opportunities sometimes
present themselves when you least
expect it. 

MASTERCLASS
11
ANNA WINTOUR

Case Studies: Lessons


From Creative Leaders

anna’s tips

Have a broad range of experience

Know and love your audience

Stay engaged with the wider world beyond your own industry

Times will be tough. Stay true to your vision.

E v e ry s u c c e s s s to ry i s d i ff e r e n t,
but Anna highlights three fashion designers who 30

have inspired her and whose careers she feels


serve as great examples of different paths to
success: Christopher Bailey, Michael Kors, and
Miuccia Prada. 
“Even though they are
designers specifically, each has a
lesson that is relevant for you to
know and understand as a creative
leader, no matter the type of work
that you are engaged in.”

MASTERCLASS
11 / Case Studies: Lessons From Creative Leaders ANNA WINTOUR

HOW TO LEARN FROM INDUSTRY LEADERS


CHRISTOPHER BAILEY AT BURBERRY: MIUCCIA PRADA AT PRADA:
Understand your brand and leverage Don’t be afraid of reinvention. 
that to the hilt.

Miuccia Prada took over her family’s staid luggage brand


Bailey spent more than a decade working at other design in 1978, and, through her bold, creative point of view, she
houses—including Donna Karan and Gucci—before taking was able to transform Prada into one of the world’s most
over as creative director at Burberry in 2004. He is credited recognizable brands. She began by making handbags
with transforming the fortunes of the historic British brand out of black nylon (until then, an overlooked material) and
and evolving it from a 150-year-old trench coat company turning them into a covetable accessory. After launching
into a global power player in the luxury market. handbags in 1985, she introduced her first womenswear
collection in 1989. Not only was Prada able to inject new life
Bailey did this by identifying what was key to the DNA of the into an old idea, but she’s always had a knack for isolating
brand—its Britishness, among other things—and embracing key cultural and political moments and infusing those into
them as core tenets. In 2009, he successfully fought to her collections. When Prada saw the trends moving toward
move the brand’s fashion show from Milan to London. casual (but still sophisticated) clothing, she launched her
That move helped turn London Fashion Week, previously Miu Miu line—her nickname—which was inspired by her own
a sleepy weekend on the calendar that most editors and wardrobe.
buyers skipped, into an essential stop between New York
and Milan. Showing in London made Burberry Burberry, but Prada designs clothes for the thinking woman (and man) 31
it also made London Fashion Week what it is today. Bailey because she is thinking when designing them. Not only
also tapped young, on-the-verge British models and actors does she design the brand’s men’s and women’s lines as
such as Cara Delevingne and Emma Watson to star in his well as Miu Miu, she also oversees the Fondazione Prada, a
campaigns.  contemporary art institution that opened in Milan in 2015
and was designed by Rem Koolhaas’ OMA. Bar Luce, the
Bailey has also stayed true to his own personal brand—he gallery’s Milanese-style cafe, was designed by beloved
is married to British actor Simon Woods and was the first director Wes Anderson (Isle of Dogs, The Grand Budapest
openly gay executive of an FTSE 100 company (the U.K. Hotel, The Life Aquatic With Steve Zissou). An exhibition
equivalent of the Dow Jones Industrial Average). In 2017, curated by Anderson and his wife will be on display at the
Bailey announced he was stepping down from Burberry, Fondazione from September 20 of this year through January
following his instincts that it was time to take a sabbatical. 13 of 2020.
In a March 2018 interview with Vogue.com, Bailey said he
was planning to use his newfound freedom to spend time
with his husband and their two daughters, Iris and Nell, at
their home in north London. Riccardo Tisci succeeded him
that same year. 

MASTERCLASS
11 / Case Studies: Lessons From Creative Leaders ANNA WINTOUR

MICHAEL KORS: Kors’ trajectory is proof that unexpected pivots are some-
Stay true to yourself and your customer, times necessary. But it is essential to keep your eye on your
end goal. Kors always engaged with his customer with
no matter what.  panache, meaning women wearing Michael Kors felt they
had their own personal connection to the designer. (His
five-season tenure as a judge on Project Runway also helped
Throughout his long and sometimes bumpy career, Kors with that impression.)
has neither strayed far from his brand values nor the tastes
of his customers. He is designing for them because he loves Like Bailey and Prada, Kors does not wear fashion blinders.
them. After launching his line at Bergdorf Goodman in He is open to and inspired by the world around him. Kors
1981, Kors was forced to shutter his KORS brand in 1993 is a theater lover who has been known to attend Broadway
due to his licensing partner filing for Chapter 11 bankruptcy. shows up to three times a week, and that seeps into his
It took him a few years to get back on his feet, which he work: Tony nominees are often outfitted in his designs, and
achieved by launching a more affordable line and by taking in some of his more recent fashion shows, he has included
the design helm at Celine. His success there bolstered his a performance to amplify the themes of the collections
credentials for his own brand, and he left Celine in 2003 to (Sara Bareilles sang “Dock of the Bay” as he showcased his
focus on Michael Kors full-time.  beach-themed Spring/Summer 2018 collection). 

32

MASTERCLASS
12
ANNA WINTOUR

Leading With Impact

It is important to always be thinking career you decide to take,” Anna says, “there is
about how you can have the biggest impact on an innate sense of responsibility, of giving back
your industry and lend the most support to those to the world, of understanding what you care
in need. You should always try to use your plat- about and what you can do…. Engage with
form to do the most good. Perhaps this means whatever is happening in the world in a thought-
raising awareness or funds for a particular cause, ful way, and stand up for what you believe is right.
as Anna did on behalf of the AIDS crisis with the Take a point of view, and be thoughtful about it,
7th on Sale initiative, which raised much-needed and stand by your convictions.”
funds, or as she continues to do with the CFDA/ Another mark of a successful leader is
Vogue Fashion Fund. Perhaps it means thinking fostering transparency with your audience. The
on a global scale: When the economy faltered September Issue, R.J. Cutler’s 2009 documen-
in 2009, Anna—along with tary charting the production of 33

the CFDA and Mayor Michael “I think about how we Vogue’s annual September issue
Bloomberg—created Fashion’s can use Vogue as a (the largest of the year), was an
Night Out, an event intended to platform for change, a important moment for Anna and
bring recession-stung consum- platform for activism, Vogue because it revealed the
ers into more than 800 stores a platform, very inner workings of one of the most
across New York’s five boroughs. importantly, for the prestigious magazines in the
By 2010, the event had expanded fashion industry.” world. It was especially import-
into 500 cities nationwide and ant following the release of The
30 cities internationally and continues to this Devil Wears Prada three years earlier, which many
day around the world in cities like Sydney, Madrid, people understood to be an accurate depiction
and London. of life at Vogue (it was not). In this age of social
Or perhaps impacting your industry means media and reality television, it can be especially
responding to an especially divisive cultural beneficial to provide insight to both your team
moment, as Anna did by highlighting narra- and your audience about your process. As a
tives surrounding activism, hope, and change leader, think creatively about different ways
after the 2016 presidential election. “Whatever to do this and which method makes the most
you’re doing—whatever path you choose or what sense for you, your role, and your brand. Since

MASTERCLASS
12 / Leading With Impact ANNA WINTOUR

granting unprecedented access to Cutler during days, editors, designers, executives, photogra-
The September Issue, Anna has continued to open phers, models, and celebrities share their stories
up to audiences through the 2016 documentary through in-depth conversations in front of a live
The First Monday in May and more recently in audience. The conference draws attendees as
Vogue.com videos like her Go Ask Anna series disparate as 60-something industry veterans
(which gives viewers the chance to ask her their and 18-year-old students from Parsons School
questions). This openness can help your audi- of Design and demonstrates how important
ence and your team feel more connected to both it is to look for opportunities to engage your
you and your work.  audience in new and unexpected ways. Always
The Forces of Fashion conference, founded in try to be thinking ahead and anticipating the
2017 and recurring annually in October, plays a different ways people may want to engage
similar role as The September Issue did for those with your brand, then deliver that to them while
interested in fashion and media. Over two remaining true to your brand’s DNA.

CONCLUSION
The media world has changed drastically in the nearly 50
34
years since Anna began working in publishing. But the
lessons she imparts in this class go beyond fashion and
journalism. They can be applied to any industry to help
creative leaders identify what is most important to them,
what their brand is, and how they can best execute on their
mission. Creativity is a wonderful gift, but without the tools
to harness and apply that creativity, it can easily be lost or
squandered. Use what you’ve learned from Anna to become
the best leader, learner, and visionary you can be. 

Recommended Viewing 

The September Issue, directed by R.J. Cutler


The First Monday in May, directed by Andrew Rossi

MASTERCLASS
ANNA WINTOUR

CREDITS
CHAPTER ONE | INTRODUCTION Art and Music by

Annie Leibovitz Eric Boman Horst P. Horst Steven Klein


Arthur Elgort George Hoyningen-Huene Jonathan Becker
Charlotte Wales Gordon Von Steiner Monty Coles

CHAPTER TWO | GETTING THE WORK DONE: ANNA’S MANAGEMENT TIPS Art and Music by

Mario Testino

CHAPTER THREE | FINDING YOUR VOICE AND SUCCEEDING Art and Music by

Annie Leibovitz

CHAPTER FOUR | LEADING WITH A VISION Art and Music by

Angelo Pennetta Mikael Jansson Steven Meisel Zoe Ghertner


Martin Parr Patrick Demarchelier Van Lamsweerde Inez & Matadin Vinoodh

CHAPTER FIVE | EDITORIAL DECISION-MAKING Art and Music by

Patrick Demarchelier Short White Wedding “Director: Ujin Lin Stefan Ruiz Van Lamsweerde Inez & Matadin Vinoodh
Angelo Pennetta Fashion Editor: Jorden Bickham “ Stephen Shore
Annie Leibovitz Patrick Demarchelier Steven Klein
Becky Kolsrud Pierre Scherman Tierney Gearon

CHAPTER SIX | EXECUTING A VISION: TRANSFORMING THE MET GALA Art and Musci by

Paolo Roversii Heavenly Bodies invitation images courtesy Camp invitation courtesy of the
of The Metropolitan Museum of Art Library of Congress

CHAPTER SEVEN | PHOTOGRAPHY THE POWER OF AN IMAGE Art and Music by


35
Alas Mert & Piggott Marcus David Luraschi Nigel Shafran Tierney Gearon
Annie Leibovitz Deborah Turbeville Oliver Hadlee Pearch Toni Frissell
Anton Corbijn Ethan James Green Patrick Demarchelier Tyler Mitchell
Arthur Elgort Herb Ritts Patrick Lichfield Van Lamsweerde Inez & Matadin Vinoodh
Bert Stern Horst P. Horst Peter Lindbergh William Klein
Bibi Cornejo Borthwick Jackie Nickerson Richard Avedon Zoe Ghertner
Charlie Engman Jamie Hawkesworth Steven Klein
Craig McDean Mikael Jansson Steven Meisel

CHAPTER EIGHT | EVOLVING A BRAND: A LOOK BACK AT ICONIC VOGUE COVERS Art and Music by

Annie Leibovitz Mario Testino Richard Avedon Tyler Mitchell


Herb Ritts Patrick Demarchelier Sean Thomas Van Lamsweerde Inez & Matadin Vinoodh
Irving Penn Peter Lindbergh Steven Meisel

CHAPTER NINE | DESIGNERS: WHAT IT TAKES TO SUCCEED Art and Music by

Alas Mert & Piggott Marcus Alex Dolan Gordon Von Steiner Norman Jean Roy
Alasdair Mclellan Alex Webb Mikael Jansson Tierney Gearon

CHAPTER TEN | SPOTTING DESIGNER TALENT: CFDA/VOGUE FASHION FUND Art and Music by

Andrew Jacobs Casey Kelbaugh Christopher Garcia Valle Jackie Kursel

CHAPTER ELEVEN | CASE STUDIES: LESSONS FROM CREATIVE LEADERS Art and Music by

Alas Mert & Piggott Marcus Bruce Weber Mario Testino


Annie Liebovitz Hannah Thomson Patrick Demarchelier

CHAPTER TWELVE | LEADING WITH IMPACT Art and Music by

Gordon Von Steiner Lee Miller The Selby Studio


Keith Harring Patrick Demarchelier Van Lamsweerde Inez & Matadin Vinoodh

MASTERCLASS