The Creative Class | Simon Doonan, Creative Ambassador

NEW YORK, United States — "I'm always looking for what really moves the needle," Simon Doonan, Barneys New York creative ambassador-at-large, told BoF. "That's where the power is."

Doonan has built a legendary career on camp: his famously eccentric store window displays have featured Margaret Thatcher as a dominatrix, unused colostomy bags pinned to the walls and a Marcel Duchamp urinal amongst Yohji Yomamoto outfits. His satirical style columns come with titles like "Should Old People Wear Sassy Underwear?" and "Are Fat Men More Trustworthy?" Then there's the shelf's worth of cheeky, humour-driven books he's published in the last decade or so — Madonna bought the film rights to his first, Confessions of a Window Dresser — as well as his cameo appearances on America's Next Top Model and Gossip Girl.

But “there was never any long-term goal in mind,” Doonan notes. “It was just a roll of the dice.” He’s been a vital and enduring part of the Barneys New York DNA for 27 years now, but admits, “I never thought, ‘I’ll end up in America in a department store.’”

Doonan grew up humbly in Reading, a town outside of London, in the 1950s and 1960s. “It’s known for two things. Oscar Wilde was in jail there ( see “The Ballad of Reading Gaol”) and Marianne Faithfull went to the convent school I went to. But it was kind of grim,” he recalls. “All of my relatives were insane or alcoholic. We didn’t have a lot of money and the future didn’t look great. The truth of the matter for me was, the minute I was 16, I had to go and get a job in a factory.”

I saw this shimmering mirage of fashion. It seemed transformative, like you could embrace fashion and transcend your circumstances.

Doonan's first job was in the same cork factory where his mother worked, collecting and hauling punched-out corkboards; later, he did demolition work on public toilets. But the seeds of his future were already being planted. “[When] I was a teenager in the Swinging Sixties, magazines and newspapers started to cover the new style revolution — the mod revolution. I remember seeing that first picture of Twiggy that Barry Lategan took — [her] in a Fair Isle sweater — in the newspapers,” Doonan says. “You felt like something big was happening. Before that, fashion was sort of the prerogative of wealthy people. Older, patrician people. And then it shifted and it was all about youth. ”

At 21, Doonan moved to London, doing sales in a dress shop on Bond Street and then landing his first window-dressing job, at British heritage brand Aquascutum. “I saw this shimmering mirage of fashion. It seemed transformative, like you could embrace fashion and transcend your circumstances. For me, fashion was like a lifeline, where you could grab onto something and connect with this other world and get out of the world you were in."

Doonan has never left his roots behind, however — he credits his upbringing for his famously quirky sense of humour. "Piss-taking, it's a big part of being English — not taking things too seriously, debunking things." Plus, he notes, "my parents are really funny. They always subscribed to satirical magazines like Private Eye. They loved satire and Monty Python."

One day, Doonan was on freelance assignment, doing one of his signature "transgressive, nutty windows" for Tommy Nutter, "the trendy tailor on Savile Row in the 70s, because he made Mick Jagger's wedding suit when Mick got married to Bianca." While installing the display, which featured taxidermy rats in diamond chokers — "I would think of the things people would never do in a window, and do that," Doonan explains — "this guy came in and said, 'You should come work for me. That was Tommy Perse, who owns Maxfield." A few months later, 25-year-old Doonan headed to Los Angeles to take Perse up on his offer, and remained at Maxfield for the next eight years. "He was great to me — a very creative, wonderful, brilliant guy, and I did insane windows there."

In 1985, Diana Vreeland hired Doonan to do the displays for her "Costumes of Royal India" event at the Costume Institute in New York. It was a five-month experience that influenced and reinforced Doonan’s own unconventional approach.

"I learned a lot. Vreeland, what she was so brilliant at, she understood fancy and posh, but she was in her heart of hearts a rule-breaker and a punk rock person," recalls Doonan. "She understood who Coco Chanel was and what she represented. She was a friend of hers. But she also understood why it was great to wear fluorescent Dynel wigs. Breaking taboos was very important for her. And so I thought, 'Oh, you can do both.' She understood that fashion was more than just being posh and having money. It was how important it was to be creative."

Doonan “scraped together my meagre earnings” and bought “a $100 dessert ticket” to the exhibit’s opening, where he was introduced to Gene Pressman, owner of Barneys New York. “Gene said to me, ‘Oh, I know who you are, you do those crazy windows at Maxfield. You should come work for me.’”

Shortly thereafter, Doonan joined Barneys when it was a single store in downtown New York — and has been there ever since. "I always thought the Pressmans did such a mitzvah, putting a roof over my head. They became a big surrogate family for me. I was getting so much back, working with architects like Peter Marino and Andrée Putman and meeting designers, everybody from Jil Sander to Alaia, Miuccia Prada. All these people came into Barneys first. Dries van Noten, Margiela. You could only buy that stuff at Barneys in the 80s and 90s. So I had this incredible window into fashion through this job. It became a dream job."

For many years, Doonan served as Barneys' creative director, infusing the store's luxe sensibility with his subversive humour. "I thought, Barneys has quality and luxury and designer merchandising and fashion, but there's no reason that the windows have to surrender to that idea in some kind of expected way. I always wanted to create that juxtaposition between this playful, Coney Island, Monty Python exterior, and then inside is the luxury."

Indeed, Doonan took that idea of “thinking high-low, not having preconceived ideas about everything” further than just the store’s windows. “Advertising was a big responsibility for me for years, and special events, and all aspects of the Barneys image. You know, once you start to think that way — taking things out of context — then that kind of creativity applies to anything.”

Doonan also began exploring a new way to express his ideas: writing. "Even though I had gotten into college, I still thought of myself as fundamentally an idiot," he says. "Plus, [I was] a visual person. So I never put pen to paper." But after reading the introduction to his 2001 book, Confessions of a Window Dresser, his publisher "said 'You're hilarious and insane. You need to write more.'"

That, coupled with The New York Observer's offer of a style column right after the book's release, convinced Doonan. "It was one of those opportunities that come along that I just think, 'Yes, that's what I should do now.'" Currently, he has under his belt a decade of columns at the Observer, an ongoing column at Slate and six books (a seventh is due out this fall).

Since 2011, when Doonan was made Barneys' creative ambassador-at-large after a management change that saw former Gucci chief executive Mark Lee take the reins at the store, Doonan's role at the retailer has become "very different, because it's not so task-oriented," he explains. "I'm so familiar with the company, the brand, the vendors, the customers, that it's about connecting with all those different communities. Like this week I'm going to Scottsdale with Lisa Perry — we're doing events there with customers. Last week I was in LA — we had a big Belstaff event, we did some events for the Academy Awards. So it's lots of travel, lots of event-oriented and press stuff. It's always been easy for me to talk to the press — I always understood what they wanted: something cheeky, a different angle. They don't want your press release stuffed down their throat."

Ultimately, he says, “My goal is to be creatively satisfied, to have fun, and to feel good every morning. I approached the world with very low expectations, and I was very pleasantly surprised.”

As for those looking to break into fashion, Doonan advises, “If you work hard, things will fall into place. Let things unfold. You never know!”