Big Idea: Create a fashion hub at New York's Lincoln Center, which Stephanie Winston Wolkoff calls a "blank white canvas that hadn't been filled." "We need to incorporate fashion into every element and institution," she says, "whether it be through designer-lecture series, photography exhibitions, or collaborative efforts between artists and designers." Wolkoff is starting with Mercedes-Benz Fashion Week, which this month relocates to Lincoln Center from Bryant Park. Much as Lincoln Center has tried to diversify the audience for performing arts, the fashion-week director plans to democratize the typically insider-only event, via programs for designer-loving everyday Janes, including a Vogue consumer fashion show for 1,000 non-industry people featuring clothes that are actually available in stores.
Credentials: Remember how Emily Blunt flanked Meryl Streep's Anna Wintour-inspired character in The Devil Wears Prada, whispering names to her at the Metropolitan Museum of Art's Costume Institute Gala? Wolkoff was a real-life Wintour whisperer. She worked for 11 years as Vogue's director of special events, handling logistics — and, yes, all those names — for those galas at the Met.
Gala as brainteaser: Organizing the Costume Institute ball "was like a chess game. I knew every detail about every person at every single seat. I worked with other editors to decide what guest was wearing what, so they wouldn't come in the same dresses. I made sure exes weren't seated with exes."
Devil Wears Prada moment: Wolkoff says that all the Vogue girls had to do menial tasks such as getting coffee and retrieving dry cleaning. Her most memorable task: "I was in London doing Unforgettable: Fashion of the Oscars," a charity auction to raise money for AIDS research. "I was with Natasha Richardson, and I was sweeping the floor in my ball gown."
Why she left Vogue last year: Leading up to big events such as the Costume Institute Gala, Wolkoff would run home to tuck in her three kids — now ages 8, 6, and 3 — and then sprint back to work until 2 or 3 a.m. Her most recent maternity leave lasted a week. "I resigned five times. Anna would say, 'Stephanie, you're not going to want to do this. Take some time. Get some rest.' " Wintour was right four times, but in the end, Wolkoff says, "I was really tired of trying to juggle three kids and be the perfect mom."
The Supermom myth: Wolkoff says her experience as a working mother taught her "there's no such thing as Supermom. I thought I could have the best of both worlds, except the guilt inside of me took over."
The lessons of her three-month "retirement": "I learned not to be so obsessive-compulsive about needing to finish everything that day. I realized we're all perfectly imperfect, which was a big thing. Perfectionism, to me, was an important thing." She also realized she needs to work: "I have ambition and drive, and I'm passionate about the fashion industry."
Email or phone? Email. "At least 275 in a typical day."
BlackBerry or iPhone? BlackBerry. "Indispensable!"
Style icons: Wolkoff says that style icons, to her, are people whose fashion choices are appropriate "to their body and lifestyle." Three names come to mind: Jacqueline Kennedy, Babe Paley, and Sophia Loren.
Childhood outfits: Sports uniforms. "I was never into fashion. I was a tomboy!" The 6-foot-1 Wolkoff played Division I basketball at Fordham. "I tried out for the Olympics, was an All-American lacrosse player, and a black belt in karate."
A model for democracy in fashion: Vera Wang. "She does high-end with bridal and more moderate at Kohl's. Plus, all her tabletop is reasonably priced."
What her kids wear: "I believe kids should dress for their age, and for now, it's all about comfort." Her boys, she says, "live in Crewcuts by J.Crew and Ralph Lauren." She confesses that she loves to "put my little girl in gorgeous dresses. I love Jacadi for her."
What would you wear if nobody were looking? "Nothing! Actually, I live in T-shirts and True Religion jeans."
A gown to remember: Wolkoff says that one of the most fabulous things she's worn is the Vera Wang dress she chose for this year's Costume Institute Gala. "The navy satin with jeweled shoulders was beautiful but understated," and she praises the "fine lines and ruched material. The dress matched the affair."
Life lessons from Anna Wintour: Wolkoff says she learned two key things from the editrix and mom of two, whom she calls her career role model: "That you actually can have a balance between family and career. And to follow your instincts."
A version of this article appeared in the September 2010 issue of Fast Company magazine.