Meet Melania's Former Senior Adviser
In January 2017, the Washington Post reported that first lady Melania Trump's first hire in the White House was Stephanie Winston Wolkoff as senior adviser. The New York Post said Winston Wolkoff – an event planner who helped produce President Donald Trump's inauguration – would be chief strategist. But in February 2018, Politico reported that Winston Wolkoff was actually serving as a “contracted volunteer” through a special arrangement with the White House, and later that month news broke that her contract had been terminated. The former Vogue staffer, a longtime friend of Melania’s, helped style her wardrobe and assisted with the execution of some of the first lady’s initiatives. A company she founded in December 2016 also reportedly received millions of dollars for its work on the inauguration. Here's everything else you need to know about her:
1. She has a few things in common with the first lady.
They are both 47 years old. They are both beautiful. They are both tall: Trump is 5-foot-11 and Winston Wolkoff is 6-foot-1. These days, they both favor the same hairstyle: long, golden caramel hair curled into soft waves. And, like Donald Trump used to be, Winston Wolkoff's husband, David Wolkoff, is a real estate developer in New York. Wolkoff is best known for whitewashing and demolishing the Queens graffiti landmark 5Pointz.
Melania Trump and Winston Wolkoff have been acquainted for 20 years. They were close enough that they met every month for lunch, according to a profile in the New York Times. Trump was a guest at Winston Wolkoff's 40th birthday bash, along with Jessica Seinfeld and the publicist Peggy Siegel. The first lady told the Times that Winston Wolkoff "has a way of connecting with people - motivating them to get the job done in the best way possible."
They also share a friend in designer Rachel Roy, who many suspected was the "Becky with the good hair" that Beyoncé called out in Lemonade.
2. She comes from the fashion world.
For 11 years, Winston Wolkoff worked in public relations and events at Vogue, then went on to oversee New York Fashion Week at Lincoln Center before opening her own consulting firm, SWW Creative.
Winston Wolkoff's entry into fashion happened by chance. She studied communications in college and was an athlete, playing basketball for two years in college. In the late '90s, she was working at Sotheby's when she met two editors from Vogue at a dinner, according to a career interview she did with Brand x Ed x U. Shortly after that, she was recruited by the magazine to be a public relations manager, but she knew little about fashion or her future boss.
"I just didn't understand what it meant to wait around to meet with Anna Wintour," Winston Wolkoff told the Observer about her job interview with the magazine's editor-in-chief. "I didn't lie that I read Vogue every day or that I grew up loving fashion, but I did know how to roll up my sleeves and do whatever it took to learn it."
That same day, Winston Wolkoff was offered the job and she accepted. "I didn't hesitate," she said in her Brand x Ed x U interview.
At Vogue, Winston Wolkoff went from being public relations manager to director of special events. She oversaw the annual Costume Institute Gala at the Metropolitan Museum of Art, the marquee fashion party of the year, and was quoted in a New York magazine article saying something that won't stop following her around: "No money, no come-y."
She had the daunting task of arranging the seating chart. According to New York, Winston Wolkoff once had to put Jennifer Lopez and Marc Anthony, then dating but not out publicly as a couple, at different tables but with their backs to each other so they could still talk.
And then there were all the people she had to turn away. "My phone rings off the hook and I have to say, 'Look, I have 100 people on the wait list - people Chanel cares about, Vogue cares about, the Met cares about, but there's just no more room."
When she got to Lincoln Center, Winston Wolkoff described herself as a "professional multitasker" in an interview with 1stDibs. "I function as a metaphoric intercom, planner, sounding board, and all-around public relations rep for the fashion industry."
3. Anna Wintour was her mentor.
When she worked at Vogue, Winston Wolkoff sat outside Wintour's office - within shouting distance, according to New York. Wintour was the key to Winston Wolkoff's fashion education and her rise in the industry, and Winston Wolkoff made sure to pay respects to her career sponsor at every opportunity.
"Anna Wintour truly opened my eyes to creativity, and taught me how to think and work outside the box, encouraging me to question limits and eventually inspiring me to start my own company," Winston Wolkoff told Refinery29.
"I didn't know any of this before Anna taught me," she told New York about the intricacies of a good seating chart.
"I had a complete, open, hands-on approach with the greatest mentor (in my opinion) within the industry," Winston Wolkoff said in an interview with Dolce magazine. "Anna [Wintour] really enabled me to take things to the next level."
"I respect Anna the most," she told the Observer in 2012, after she had left Vogue.
What's potentially awkward now is that Wintour vocally and passionately supported Hillary Clinton for president, and her former protégée, after once donating $10,000 to the Democratic National Committee in 2014, has gone to work for the other team. Perhaps it's the result of another lesson from Wintour that Winston Wolkoff absorbed: "One other big thing I learned from Anna is that relationships are everything," she told Dolce. "People say when one door closes another opens, but for me it's a continuum of opening doors. You don't want to close any."
4. Winston Wolkoff is very wealthy - and she isn't shy about it.
Along with her husband and their three children, two boys and a girl, Winston Wolkoff lived in a Park Avenue apartment on New York's Upper East Side until 2014. That home, which sold for $10 million, was 4,000 square feet, according to the Wall Street Journal, and featured a "private elevator entrance." Winston Wolkoff's closet and wardrobe were photographed for the Wall Street Journal, Harper's Bazaar, The Coveteur, and Refinery29. She has at least two personal assistants, a publicist, nannies, and once employed an "academic and self-management coach" for her teenage son.
The Wolkoffs were married in 2000 in an extravagant wedding at the Pierre Hotel, stomping grounds of Gossip Girl characters. Here's an excerpt from the couple's New York Times wedding feature:
Violinists serenaded 300 guests at the Pierre in Manhattan, where the ceremony took place in a ballroom resembling one in a storybook castle. It was decorated with tall, gilded candelabra that were overgrown with flowers in muted antique tones. The huppah, or Jewish wedding canopy, was made of heavy velvet and trimmed on top with swags, tassels and a two-foot crown of flowers. It was as ornate as a jewel box and as big as a studio apartment.
She runs with a crew of other Upper East Siders called "the socials," according to New York, people who can and do pay thousands of dollars to attend the Met Gala. Among them? Trump's treasury secretary nominee Steven Mnuchin.
5. But she wasn't always so wealthy.
Winston Wolkoff grew up in the Catskills, according to the New York Times, and was born Stephanie Batinkoff. She is estranged from her biological father, Barry Batinkoff, and was later adopted by Bruce Winston, diamond jeweler Harry Winston's son, after he married her mother. Winston Wolkoff changed her last name from Batinkoff to Winston and started "being described in news reports as the granddaughter of Harry Winston, an 'heiress who grew up in Scarsdale,'" according to the Times.
In 2010, after being described as such an heiress in the Times, the New York Post published a response. "Stephanie is a Batinkoff of the successful Catskills chicken-farming family," said the lawyer for her father Barry's brother. "She did not grow up on the Winston estate in Scarsdale."
6. She has struggled to balance career and family.
When she left Vogue after 11 years, Winston Wolkoff intended to break from her career and focus on her family. She had burned out after grinding for so long: "I was really tired of trying to juggle three kids and be the perfect mom," she told Fast Company.
Three months later, Wintour recruited Winston Wolkoff to become the first director of fashion for Lincoln Center, where she would spearhead the relocation of New York Fashion Week. "I drop the kids off at school every day, regardless of the show schedule," she wrote in the Huffington Post. "Life goes on for them even while Mercedes-Benz Fashion Week steamrolls my appointment book; the car rides mean that I don't miss what's at home for the sake of what's on the runway."
She left that job after 2 1/2 years to launch SWW Creative in 2012 - and continued juggling. "I go to sleep once I've put my third child to sleep, and I will wake up around 1 o'clock in the morning and work for a couple of hours, and then go back to bed," she told the Observer.
6. She is always perfectly put together.
"She's immaculate," Wintour said of Winston Wolkoff in the New York Times. "She makes everyone else feel like a complete mess." During her interview with 1stDibs, "not a long chestnut-colored hair is out of place" on Winston Wolkoff. Estée Lauder group president John Demsey told the New York Times that Winston Wolkoff is "perfectly blown out."
Her style is classic and expensive. She has a collection of Birkin bags and label-checks Ralph Lauren, Vera Wang, Michael Kors, Céline, Prada, Lanvin, Dennis Basso, and Alexander McQueen. "I try to keep my appearances classic and sophisticated," she told Harper's Bazaar. "Style depends more on how you carry yourself in the clothes than the clothes alone, but a killer pair of heels doesn't hurt."
7. She takes pride in her work ethic and organization.
When she was still at Vogue, Winston Wolkoff's office was covered in "700 Post-it notes," according to New York. Her children's schedules are color-coded and they each had their own bulletin board for their schedules at their Park Avenue apartment.
Wintour nicknamed her "General Winston" for the way she could "draw up a plan, marshal her forces ... until she'd seen the project through and completed it to her satisfaction," Wintour told the Wall Street Journal.
"I stay in control of every little thing," Winston Wolkoff told 1stDibs. "I want to make sure that nothing falls through the cracks."
When she launched SWW Creative, Winston Wolkoff told Forbes that the work never stopped. "We work until about 4 o'clock in the morning. It's around the clock."
She has a reputation for being business-minded. Winston Wolkoff "brought corporate crisp efficiency" to the Met Gala, according to the New York Times. When she got to Fashion Week, she brought her corporate sensibilities along. According to the Observer, Winston Wolkoff "rankled fashion's artistes, who feel that recent changes have given the event a noticeable odor of commerce."
8. She helped orchestrate Trump's wardrobe as first lady, including her inauguration looks.
Winston Wolkoff leveraged her fashion connections to put together Trump's inauguration wardrobe, which included pieces by Ralph Lauren and Reem Acra. "It was an honor to connect dear friends and the greatest of American talent to recognize and honor the beauty and grace of our new first lady," Winston Wolkoff told WWD. She even stepped up to speak for Trump when critics called her out for wearing European designers.
"Mrs. Trump is a proud and longtime supporter of American fashion," Winston Wolkoff told the Times. "Mrs. Trump buys from an international mix of brands because that is what reflects her uniquely American life experience and style. She is more excited than ever to make a platform for American designers as she did on one of the most important weeks in history, the Inauguration, showcasing the extraordinary talents of American designers."
9. Her contract was terminated after about a year.
Winston Wolkoff’s position in the White house was technically as a “contracted volunteer,” which means that she didn't get paid, according to Politico. But she garnered criticism for having a government-issued phone, computer, and badge granting her access to the West Wing when she didn't even live in Washington, D.C. She visited the White House every few weeks, according to two White House officials.
Meanwhile, a little over a year after Winston Wolkoff took her post, the New York Times reported based on tax disclosures filed with the Internal Revenue Service that a company called WIS Media Partners, created by Winston Wolkoff just six weeks before the inauguration, received $26 million for planning the event, some of which likely went to subcontractors. Winston Winkoff reportedly received $1.62 million of that, although officials on the inauguration committee told the Times that she used that money to help pay other inaugural workers.
In late February 2018, the New York Times reported that her contract had been terminated. “We thank her for her hard work and wish her all the best," Melania's spokeswoman Stephanie Grisham said.
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